Sodium Hydroxide → HCID 59270966, compound

HRID 1965919Notes

Reaction equation

HRID 1965919 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]1[C:19]2[N:18]([CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25]3[CH:26]=[C:27]([CH:102]=[C:103]([O:123][CH2:124][CH2:125][CH2:126][CH2:127][N:128]4[C:140]5[CH:139]=[CH:138][CH:137]=[CH:136][C:135]=5[C:134]5[C:129]4=[CH:130][CH:131]=[CH:132][CH:133]=5)[C:104]=3[O:105][CH2:106][CH2:107][CH2:108][CH2:109][N:110]3[C:122]4[CH:121]=[CH:120][CH:119]=[CH:118][C:117]=4[C:116]4[C:111]3=[CH:112][CH:113]=[CH:114][CH:115]=4)[CH2:28][O:29][C:30]3[CH:31]=[C:32]([CH:37]=[C:38]([O:40][CH2:41][C:42]4[CH:47]=[C:46]([O:48][CH2:49][CH2:50][CH2:51][CH2:52][N:53]5[C:65]6[CH:64]=[CH:63][CH:62]=[CH:61][C:60]=6[C:59]6[C:54]5=[CH:55][CH:56]=[CH:57][CH:58]=6)[C:45]([O:66][CH2:67][CH2:68][CH2:69][CH2:70][N:71]5[C:83]6[CH:82]=[CH:81][CH:80]=[CH:79][C:78]=6[C:77]6[C:72]5=[CH:73][CH:74]=[CH:75][CH:76]=6)=[C:44]([O:84][CH2:85][CH2:86][CH2:87][CH2:88][N:89]5[C:101]6[CH:100]=[CH:99][CH:98]=[CH:97][C:96]=6[C:95]6[C:90]5=[CH:91][CH:92]=[CH:93][CH:94]=6)[CH:43]=4)[CH:39]=3)[C:33](OC)=[O:34])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]=2[CH:10]=[CH:9][CH:8]=1.[OH-].[Na+]>C1COCC1>[CH:55]1[C:54]2[N:53]([CH2:52][CH2:51][CH2:50][CH2:49][O:48][C:46]3[CH:47]=[C:42]([CH:43]=[C:44]([O:84][CH2:85][CH2:86][CH2:87][CH2:88][N:89]4[C:90]5[CH:91]=[CH:92][CH:93]=[CH:94][C:95]=5[C:96]5[C:101]4=[CH:100][CH:99]=[CH:98][CH:97]=5)[C:45]=3[O:66][CH2:67][CH2:68][CH2:69][CH2:70][N:71]3[C:83]4[CH:82]=[CH:81][CH:80]=[CH:79][C:78]=4[C:77]4[C:72]3=[CH:73][CH:74]=[CH:75][CH:76]=4)[CH2:41][O:40][C:38]3[CH:37]=[C:32]([CH2:33][OH:34])[CH:31]=[C:30]([O:29][CH2:28][C:27]4[CH:26]=[C:25]([O:24][CH2:23][CH2:22][CH2:21][CH2:20][N:18]5[C:17]6[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=6[C:11]6[C:19]5=[CH:7][CH:8]=[CH:9][CH:10]=6)[C:104]([O:105][CH2:106][CH2:107][CH2:108][CH2:109][N:110]5[C:122]6[CH:121]=[CH:120][CH:119]=[CH:118][C:117]=6[C:116]6[C:111]5=[CH:112][CH:113]=[CH:114][CH:115]=6)=[C:103]([O:123][CH2:124][CH2:125][CH2:126][CH2:127][N:128]5[C:129]6[CH:130]=[CH:131][CH:132]=[CH:133][C:134]=6[C:135]6[C:140]5=[CH:139][CH:138]=[CH:137][CH:136]=6)[CH:102]=4)[CH:39]=3)[C:65]3[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=3)[C:59]=2[CH:58]=[CH:57][CH:56]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 86640584HCID 86640584, compound

Product 1

HCID 59270966HCID 59270966, compoundYield 142.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

An oven-dried, magnetically stirred, 100 mL RBF was charged with a solution of LiAlH4 (9 mg, 0.141 mmol) in 40 mL freshly distilled THF. Then, a THF solution of compound 13 (0.17 g, 0.0564 mmol) was added dropwise over 0.5 hours. After stirring the reaction mixture for 2 hours at 80° C., 1 N NaOH was slowly added. The organic phase was separated and extracted with chloroform. The organics were then dried over Na2SO4 and filtered. The solvent was evaporated to give the crude product. The resulting crude product was then purified by silica gel column chromatography (eluent: chloroform:ethyl acetate=1:50 v/v) to yield 0.14 g (76%) of (3,5-bis(3,4,5-tris(4-(9H-carbazol-9-yl)butoxy)benzyloxy)phenyl)methanol (Compound 14).

Workup

  1. stirringAfter stirring the reaction mixture for 2 hours at 80° C.
  2. customThe organic phase was separated
  3. extractionextracted with chloroform
  4. dry with materialThe organics were then dried over Na2SO4
  5. filtrationfiltered
  6. customThe solvent was evaporated
  7. customto give the crude product
  8. customThe resulting crude product was then purified by silica gel column chromatography (eluent: chloroform:ethyl acetate=1:50 v/v)

Sources & evidence

ORD record
ord-de761adf6ee74f06bcd289cd942d535f
Source dataset
uspto-grants-2013_04
Patent number
US08420231B2

Reaction notes

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