Oxalyl chloride → HCID 86584593, 화합물

HRID 495341노트

반응식

HRID 495341 반응식
[C:1]([O:12][CH:13]1[CH:18]([CH:19]([CH3:21])[CH3:20])[CH2:17][CH2:16][CH:15]([CH3:22])[CH2:14]1)(=[O:11])[C:2]1[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:4]([O-])=[O:5].C(Cl)(=O)C(Cl)=O.[BH4-].[Na+].OS([O-])(=O)=O.[K+]>>[OH:5][CH2:4][C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[C:1]([O:12][C@H:13]1[C@H:18]([CH:19]([CH3:21])[CH3:20])[CH2:17][CH2:16][C@@H:15]([CH3:22])[CH2:14]1)=[O:11]

참가 물질

5

반응물 4

HCID 65578Oxalyl chlorideHCID 516920Potassium bisulfateHCID 4311764Sodium borohydrideHCID 53249597HCID 53249597, 화합물

생성물 1

HCID 86584593HCID 86584593, 화합물수율 55%

실험 절차

3.78 g (12.4 mmol) monomenthyl (−)-phthalate (Fluka) was heated at reflux in 19 ml oxalyl chloride (18 eq.) for 1.5 h. The excess oxalyl chloride was distilled under vacuum. 2.75 g crude acid chloride was then diluted in 5 ml THF cooled to −8° under argon, and 0.97 g (3 eq.) NaBH4 was added. The reaction mixture was maintained under stirring at 0° for 10 min and at ambient temperature for 30 min. The mixture was then poured over cold 5% KHSO4 then extracted using diethyl ether. Chromatography of the crude product over silica gel (93:7 toluene/ether) yielded 1.85 g (55%) pure (1R,3R,4S)-3-p-menthanyl 2-hydroxymethylbenzoate in the form of a colourless oil.

후처리

  1. distillationThe excess oxalyl chloride was distilled under vacuum
  2. addition2.75 g crude acid chloride was then diluted in 5 ml THF
  3. temperaturecooled to −8° under argon
  4. temperatureThe reaction mixture was maintained
  5. extractionthen extracted

출처 및 근거

ORD 기록
ord-d241bcd25d8149fc8072a5eb0b5367c5
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06939835B2

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