Cyclohexane → HCID 78088908, 화합물

HRID 499725

반응식

HRID 499725 반응식
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

참가 물질

7

반응물 4

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

생성물 1

HCID 78088908HCID 78088908, 화합물수율 80.1%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매2회

실험 절차

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%).

후처리

  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))

출처 및 근거

ORD 기록
ord-4fb96350c384456ebcf449f9b89690e7
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07767651B2

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