Triethylamine → Methanesulfonic acid 3-(tert-butyldimethylsilanyloxy)-2-(tert-butyldimethylsilanyloxymethyl)propyl ester

HRID 347335ノート

反応式

HRID 347335 の反応式
[Si:1]([O:8][CH2:9][CH:10]([CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH2:11][OH:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>ClCCl.O.C(OCC)(=O)C>[Si:1]([O:8][CH2:9][CH:10]([CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:16])[CH3:17])[CH2:11][O:12][S:30]([CH3:29])(=[O:32])=[O:31])([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:3])[CH3:2]

参加物

7

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 110676353-(Tert-butyldimethylsilanyloxy)-2-(tert-butyldimethylsilanyloxymethyl)propan-1-ol

生成物 1

HCID 11015147Methanesulfonic acid 3-(tert-butyldimethylsilanyloxy)-2-(tert-butyldimethylsilanyloxymethyl)propyl ester収率 97%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

Ex-13A: To a solution of 3-(tert-butyldimethylsilanyloxy)-2-(tert-butyldimethylsilanyloxymethyl)propan-1-ol (25.0 g, 74.3 mmol) and triethylamine (22.6 g, 223 mmol) in dichloromethane (150 mL) at 0° C. was added methanesulfonyl chloride (12.8 g, 111 mmol) and the resulting slurry was stirred at 0° C. for 15 min and allowed to warm to room temperature. The solution was stirred for an additional 3 h at room temperature and diluted with water (130 mL) and ethyl acetate (350 mL). The layers were separated and the aqueous was extracted with ethyl acetate (150 mL). The combined organic extracts were washed with a saturated sodium bicarbonate (200 mL), a 50% sodium chloride solution (2×200 mL), dried over sodium sulfate and concentrated to afford 29.5 g (97%) of methanesulfonic acid 3-(tert-butyldimethylsilanyloxy)-2-(tert-butyldimethylsilanyloxymethyl)propyl ester as a yellow oil. 1H-NMR (300 MHz, CDCl3) δ 4.29 (d, 2H, J=5.7 Hz), 3.61–3.68 (m, 4H), 2.99 (s, 3H), 2.04–2.11 (m, 1H), 0.88 (s, 18H), 0.049 (s, 12H). HRMS (ESI) Calcd. for C17H40O5SSi2: 413.2213 (M+H)+; Found: 413.2226.

後処理

  1. temperatureto warm to room temperature
  2. stirringThe solution was stirred for an additional 3 h at room temperature
  3. customThe layers were separated
  4. extractionthe aqueous was extracted with ethyl acetate (150 mL)
  5. washThe combined organic extracts were washed with a saturated sodium bicarbonate (200 mL)
  6. dry with materiala 50% sodium chloride solution (2×200 mL), dried over sodium sulfate
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-647185638a2a4efb8c787a5b41671c63
出典データセット
uspto-grants-2007_02
特許番号
US07173129B2

反応ノート

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