Pyridine → Carbonic acid 4-nitro-phenyl ester 1-trifluoromethyl-cyclobutyl ester

HRID 1893683노트

반응식

HRID 1893683 반응식
[F:1][C:2]([F:9])([F:8])[C:3]1([OH:7])[CH2:6][CH2:5][CH2:4]1.N1C=CC=CC=1.Cl[C:17]([O:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1)=[O:18]>ClCCl>[F:1][C:2]([F:9])([F:8])[C:3]1([O:7][C:17](=[O:18])[O:19][C:20]2[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=2)[CH2:6][CH2:5][CH2:4]1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 574451561-(Trifluoromethyl)cyclobutanol

생성물 1

HCID 57785522Carbonic acid 4-nitro-phenyl ester 1-trifluoromethyl-cyclobutyl ester수율 48.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To 1-trifluoromethyl-cyclobutanol (2.2 g, 15 mmol) in dichloromethane (7.5 mL, 2M) was added pyridine (3 mL) and 4-nitrophenyl chloroformate (4 g, 18.3 mmol). The flask was sealed and stirred at room temperature for 2 days. The reaction was diluted with dichloromethane (50 mL) and washed with 1M KHSO4(aq), saturated sodium bicarbonate, water, and brine. The organic layer was dried over sodium sulfate and concentrated in vacuo. Purification by flash column chromatography (gradient elution with 10% to 40% EtOAc in hexane) gave 2.2 g (48% yield) of carbonic acid 4-nitro-phenyl ester 1-trifluoromethyl-cyclobutyl ester as a colorless oil. 1H NMR (CDCl3, 400 MHz) δ 8.35 (d, 2H), 7.50 (d, 1H), 2.78-2.85 (m, 2H), 2.58-2.70 (m, 2H), 1.9-2.1 (m, 2H).

후처리

  1. customThe flask was sealed
  2. washwashed with 1M KHSO4(aq), saturated sodium bicarbonate, water, and brine
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification
  6. washby flash column chromatography (gradient elution with 10% to 40% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-b28046d5acea4e99853b9e7b52568a6f
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513186B2

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