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

HRID 1837092노트

반응식

HRID 1837092 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-b4481e7b48ec4186851434443bcc654c
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06780872B2

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