Sodium Hydroxide → HCID 59270963, compound

HRID 1965918Notes

Reaction equation

HRID 1965918 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:32]=[C:33]([O:53][CH2:54][CH2:55][CH2:56][CH2:57][N:58]4[C:70]5[CH:69]=[CH:68][CH:67]=[CH:66][C:65]=5[C:64]5[C:59]4=[CH:60][CH:61]=[CH:62][CH:63]=5)[C:34]=3[O:35][CH2:36][CH2:37][CH2:38][CH2:39][N:40]3[C:52]4[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=4[C:46]4[C:41]3=[CH:42][CH:43]=[CH:44][CH:45]=4)[C:28](OC)=[O:29])[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:69]1[C:70]2[N:58]([CH2:57][CH2:56][CH2:55][CH2:54][O:53][C:33]3[CH:32]=[C:27]([CH2:28][OH:29])[CH:26]=[C:25]([O:24][CH2:23][CH2:22][CH2:21][CH2:20][N:18]4[C:19]5[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=5[C:12]5[C:17]4=[CH:16][CH:15]=[CH:14][CH:13]=5)[C:34]=3[O:35][CH2:36][CH2:37][CH2:38][CH2:39][N:40]3[C:41]4[CH:42]=[CH:43][CH:44]=[CH:45][C:46]=4[C:47]4[C:52]3=[CH:51][CH:50]=[CH:49][CH:48]=4)[C:59]3[C:64](=[CH:63][CH:62]=[CH:61][CH:60]=3)[C:65]=2[CH:66]=[CH:67][CH:68]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 11542429HCID 11542429, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 59270963HCID 59270963, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
80 °C

Procedure

An oven-dried, magnetically stirred, 500 mL RBF was charged with a solution of LiAlH4 (2.2 g, 0.038 mol) in 100 mL freshly distilled THF. Then, THF solution of compound 11 (15.0 g, 0.023 mol) was added dropwise over 0.5 hours. After the reaction was maintained 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 13.2 g (92%) of (3,4,5-tris(4-(9H-carbazol-9-yl)butoxy)phenyl)methanol (Compound 12).

Workup

  1. customThe organic phase was separated
  2. extractionextracted with chloroform
  3. dry with materialThe organics were then dried over Na2SO4
  4. filtrationfiltered
  5. customThe solvent was evaporated
  6. customto give the crude product
  7. 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-98e74335a4b84c248d589a9d4421446b
Source dataset
uspto-grants-2013_04
Patent number
US08420231B2

Reaction notes

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