Isobutyric Acid → O-(1-Isobutanoyloxyethyl) S-tert-Butyl Thiocarbonate

HRID 1675978ノート

反応式

HRID 1675978 の反応式
[C:1](=[O:11])([S:6][C:7]([CH3:10])([CH3:9])[CH3:8])[O:2][CH:3](Cl)[CH3:4].[C:12]([OH:17])(=[O:16])[CH:13]([CH3:15])[CH3:14].C(N(C(C)C)CC)(C)C>CCOCC>[C:1](=[O:11])([S:6][C:7]([CH3:10])([CH3:9])[CH3:8])[O:2][CH:3]([O:17][C:12](=[O:16])[CH:13]([CH3:15])[CH3:14])[CH3:4]

参加物

5

反応物 3

HCID 6590Isobutyric Acid2 回HCID 81531DiisopropylethylamineHCID 86600957O-(1-Chloroethyl) S-tert-Butyl Thiocarbonate

生成物 1

HCID 86615734O-(1-Isobutanoyloxyethyl) S-tert-Butyl Thiocarbonate収率 90.6%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
55 °C

実験手順

Compound (3) (392 mg, 2 mmol) was dissolved in isobutyric acid (264 mg, 3 mmol) and the solution was slowly added to a pre-mixed solution of isobutyric acid (264 mg, 3 mmol) and diisopropylethylamine (387 mg, 3 mmol). The reaction mixture was heated to 55° C. for 16 h, then diluted with ether (50 mL), washed with water (2×10 mL), saturated bicarbonate solution (2×10 mL) and brine (10 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the title compound (8) as a colorless liquid (450 mg, 90%). The product was further purified by vacuum distillation (170° C./20 Torr). 1H NMR (CDCl3, 400 MHz): δ 1.16 (d, J=7.2 Hz, 6H), 1.47 (s, 9H), 1.48 (d, J=5.6 Hz, 3H), 2.53 (m, 1H), 6.90 (q, J=5.2 Hz, 1H).

後処理

  1. washwashed with water (2×10 mL), saturated bicarbonate solution (2×10 mL) and brine (10 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-bd74a28477404edab95da779aa463b8b
出典データセット
uspto-grants-2011_08
特許番号
US08003809B2

反応ノート

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