2-Methyl-3-butyn-2-ol → (1,1-Dimethylprop-2-ynyloxy)acetic acid methyl ester

HRID 1837092ノート

反応式

HRID 1837092 の反応式
[H-].[Na+].[CH3:3][C:4]([OH:8])([C:6]#[CH:7])[CH3:5].Br[CH2:10][C:11]([O:13][CH3:14])=[O:12]>C1COCC1>[CH3:3][C:4]([O:8][CH2:10][C:11]([O:13][CH3:14])=[O:12])([CH3:5])[C:6]#[CH:7]

参加物

5

反応物 3

HCID 82582-Methyl-3-butyn-2-olHCID 24758Sodium hydrideHCID 60984Methyl bromoacetate

生成物 1

HCID 13005744(1,1-Dimethylprop-2-ynyloxy)acetic acid methyl ester収率 21.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
0 °C

実験手順

A mechanically stirred suspension of sodium hydride (60% dispersion in mineral oil, 10.0 g, 0.25 mol) in THF (170 mL) at 0° C. under N2 gas was treated with 2-methyl-3-butyn-2-ol (29.1 mL, 0.30 mol) in THF (70 mL) dropwise. After stirring at 0° C. for 1 hour, the reaction mixture was treated with methyl bromoacetate (35.5 mL, 0.38 mol) in THF (100 mL). After stirring at ambient temperature overnight, the mixture was quenched into 1M HCl (300 mL) and extracted with ethyl acetate (3×300 mL). The organic layers were combined, dried over Na2SO4, and concentrated to half the volume. The residue was distilled by vacuum distillation (bp. 118-120° C./20 mmHg) to provide the tittle compound (10.0 g). 1H NMR (CDCl3) δ 1.52 (s, 6H), 2.47 (s, 1H), 3.77 (s, 3H), 4.25 (s, 2H).

後処理

  1. stirringAfter stirring at ambient temperature overnight
  2. customthe mixture was quenched into 1M HCl (300 mL)
  3. extractionextracted with ethyl acetate (3×300 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to half the volume
  6. distillationThe residue was distilled by vacuum distillation (bp. 118-120° C./20 mmHg)

出典と根拠

ORDレコード
ord-b4481e7b48ec4186851434443bcc654c
出典データセット
uspto-grants-2004_08
特許番号
US06780872B2

反応ノート

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