Triethylamine → 1-O-methanesulfonyl-2-(((1,1-dimethylethyl)diphenylsilyl)oxy)-3-(((1,1-dimethylethyl)di-phenylsilyl)oxymethyl)-1-cyclobutanol

HRID 465756노트

반응식

HRID 465756 반응식
C(N(CC)CC)C.[CH3:8][C:9]([Si:12]([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)[O:13][CH:14]1[CH:17]([CH2:18][O:19][Si:20]([C:33]([CH3:36])([CH3:35])[CH3:34])([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16][CH:15]1[OH:37])([CH3:11])[CH3:10].[CH3:50][S:51](Cl)(=[O:53])=[O:52]>C(Cl)Cl>[CH3:50][S:51]([O:37][CH:15]1[CH2:16][CH:17]([CH2:18][O:19][Si:20]([C:33]([CH3:34])([CH3:35])[CH3:36])([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:14]1[O:13][Si:12]([C:9]([CH3:8])([CH3:10])[CH3:11])([C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)(=[O:53])=[O:52]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 197943242-O-((1,1-dimethylethyl)diphenylsilyl)-3-(((1,1-dimethylethyl)diphenyl-silyl)oxymethyl)-1,2-cyclobutanediol

생성물 1

HCID 197942931-O-methanesulfonyl-2-(((1,1-dimethylethyl)diphenylsilyl)oxy)-3-(((1,1-dimethylethyl)di-phenylsilyl)oxymethyl)-1-cyclobutanol수율 60%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Freshly distilled triethylamine (1.28 g, 8.2 mmol) was dissolved in 75 mL of freshly distilled methylene chloride. To this solution was added 2.3 g (3.9 mmol) of 2-O-((1,1-dimethylethyl)diphenylsilyl)-3-(((1,1-dimethylethyl)diphenyl-silyl)oxymethyl)-1,2-cyclobutanediol from Step K and the resultant solution was cooled to -78° C. with stirring, under a nitrogen atmosphere. Methanesulfonyl chloride (0.99 g, 8.2 mmol) was added and the reaction mixture was allowed to warm to ambient temperature. After 3.5 h, the reaction mixture was diluted with 125 mL of methylene chloride and this solution was washed with 100 mL of water, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue (2.9 g) was dissolved in 25 mL of 10% acetone in hexane and purified on a 2.5×45 cm silica gel column eluted at 2 psi with 500 mL of 5% acetone in hexane, followed by 250 mL of 10% acetone in hexane, to give 1.57 g (60% yield) of the title compound; MS DCI-NH3M/Z: 690 (M+NH4)+ ; 1H NMR (CDCl3) δ 1.95 (m, 1H), 2.20 (m, 1H), 2.77 (m, 1H), 2.90 (s, 3H), 3.39 (d, 2H), 4.39 (m, 1H), 4.88 (m, 1H), 7.30-7.54 (m, l5H), 7.60-7.70 (m, 5H).

후처리

  1. washthis solution was washed with 100 mL of water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue (2.9 g) was dissolved in 25 mL of 10% acetone in hexane
  6. custompurified on a 2.5×45 cm silica gel column
  7. washeluted at 2 psi with 500 mL of 5% acetone in hexane

출처 및 근거

ORD 기록
ord-7ad789ed94fa4fe4a39e8b2f3a582d95
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05153352

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