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

HRID 465756ノート

反応式

HRID 465756 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7ad789ed94fa4fe4a39e8b2f3a582d95
出典データセット
uspto-grants-1992_10
特許番号
US05153352

反応ノート

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