Oxalyl chloride → (2R)-2-(2,4-Di-t-butylphenyloxy)propanoyl chloride

HRID 248196노트

반응식

HRID 248196 반응식
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[O:15][C@H:16]([CH3:20])[C:17](O)=[O:18])([CH3:4])([CH3:3])[CH3:2].C(Cl)(=O)C([Cl:24])=O>CN(C)C=O.C(Cl)Cl>[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[O:15][C@H:16]([CH3:20])[C:17]([Cl:24])=[O:18])([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 2

HCID 65578Oxalyl chlorideHCID 18651686(2R)-2-(2,4-Di-t-butylphenyloxy)propanoic Acid

생성물 1

HCID 53944384(2R)-2-(2,4-Di-t-butylphenyloxy)propanoyl chloride수율 99%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매2회

실험 절차

To a mixture of 675 m9 (2.2 mmol) of (2R)-2-(2,4-di-t-butylphenyloxy)propanoic acid (18) and 4 drops of N,N-dimethylformamide in methylene chloride (20 mL) at 0° C. under a nitrogen atmophere was added 1.21 mL (2.4 mmol) of a 2M solution of oxalyl chloride in methylene chloride dropwise over a 10 min period. The reaction mixture was allowed to stir at room temperature overnight. The solvent and any excess oxalyl chloride was removed by rotary evaporation and dried (under vacuum) to afford 715 mg (99%) of (2R)-2-(2,4-di-t-butylphenyloxy)propanoyl chloride (16) as a crude yellow liquid: 1H NMR (CDCl3) δ1.29 (s, 9 H), 1.42 (s, 9 H), 1.76-1.79 (d, 3 H), 4.94-5.00 (q, 1 H), 6.50-6.(d, 1 H), 7.12-7.16 (d, 1 H), 7.36 (s, 1 H); 13C NMR (CDCl3) δ175.0, 152.8, 144.1, 137.4, 124.6, 123.4, 110.6, 78.6, 35.1, 34.3, 1.5, 30.0, 18.0.

후처리

  1. customThe solvent and any excess oxalyl chloride was removed by rotary evaporation
  2. customdried (under vacuum)

출처 및 근거

ORD 기록
ord-8c9e0cd55d904bcbb902ea44eb609e28
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05208345

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