Cyclohexane → HCID 78088908, compound

HRID 499725

Reaction equation

HRID 499725 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH2:8][O:9][C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=[CH:4][C:3]=1[CH2:29][O:30][C:31]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C1CCCCC1.C([Li])(CC)C.[CH2:61]([O:68][CH:69]1[CH:74]([O:75][CH2:76][C:77]2[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=2)[CH:73]([O:83][CH2:84][C:85]2[CH:90]=[CH:89][CH:88]=[CH:87][CH:86]=2)[CH:72]([CH2:91][O:92][CH2:93][C:94]2[CH:99]=[CH:98][CH:97]=[CH:96][CH:95]=2)[O:71][C:70]1=[O:100])[C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1>C1(C)C=CC=CC=1.O>[CH2:61]([O:68][CH:69]1[CH:74]([O:75][CH2:76][C:77]2[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=2)[CH:73]([O:83][CH2:84][C:85]2[CH:86]=[CH:87][CH:88]=[CH:89][CH:90]=2)[CH:72]([CH2:91][O:92][CH2:93][C:94]2[CH:95]=[CH:96][CH:97]=[CH:98][CH:99]=2)[O:71][C:70]1([C:2]1[CH:7]=[C:6]([CH2:8][O:9][C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:5]=[CH:4][C:3]=1[CH2:29][O:30][C:31]([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[OH:100])[C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1

Participants

7

Reactant 4

HCID 8078CyclohexaneHCID 45855083,4,5-Tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-oneHCID 684580852-Bromo-1,4-bis(trityloxymethyl)benzeneHCID 178418400CID 53628100

Product 1

HCID 78088908HCID 78088908, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

Under a nitrogen stream, to a solution of 2-bromo-1,4-bis(trityloxymethyl)benzene (255.3 mg, 0.36 mmol) in toluene (1.5 ml), a cyclohexane solution of sec-butyllithium (0.99 M, 367 μl, 0.36 mmol) was added dropwise at room temperature and the solution was stirred for 30 minutes. This solution was added dropwise at −78° C. to a solution of 3,4,5-trisbenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-one (140 mg, 0.26 mmol) in toluene (1.5 ml) and the mixture was stirred at the same temperature for 30 minutes. After addition of water, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and then evaporated under reduced pressure to remove the solvent. The resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:5)) to give the titled compound (242 mg, 80%).

Workup

  1. stirringthe mixture was stirred at the same temperature for 30 minutes
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated under reduced pressure
  6. customto remove the solvent
  7. customThe resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:5))

Sources & evidence

ORD record
ord-4fb96350c384456ebcf449f9b89690e7
Source dataset
uspto-grants-2010_08
Patent number
US07767651B2

Linked notes

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