Isobutyl chloroformate → 3-[3,5-Bis(trifluoromethyl)phenyl]-1-propanol

HRID 1364650노트

반응식

HRID 1364650 반응식
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=1)[CH2:6][CH2:7][C:8](O)=[O:9].C(O)C.O.C(=O)=O.ClC(OCC(C)C)=O.[BH4-].[Na+]>C1COCC1.O>[F:1][C:2]([F:18])([F:19])[C:3]1[CH:4]=[C:5]([CH2:6][CH2:7][CH2:8][OH:9])[CH:11]=[C:12]([C:14]([F:15])([F:16])[F:17])[CH:13]=1

참가 물질

7

반응물 4

HCID 62365Isobutyl chloroformateHCID 12680983,5-Bis(trifluoromethyl)hydrocinnamic acidHCID 4311764Sodium borohydrideHCID 86603989Ethanol water dry ice

생성물 1

HCID 534343813-[3,5-Bis(trifluoromethyl)phenyl]-1-propanol

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 3,5-bis(trifluoromethyl)hydrocinnamic acid (1.0 g, 3.5 mmol) and TEA (0.46 g, 4.5 mmol) in THF (16 mL) was cooled to −40° C. (ethanol-water/dry ice bath). To this mixture was dropwise added isobutyl chloroformate (0.56 g, 4.1 mmol) and stirring was continued for another 1.5 hours while the temperature of the cooling bath was maintained between −40° C. and −20° C. Solid NaBH4 (0.53 g, 14 mmol) was added, followed by H2O (1.3 mL). The cloudy mixture was stirred overnight while warming to room temperature. After concentrating in vacuo, the residue was partitioned between ethyl acetate and water. The aqueous layer was acidified to pH 1 with 37% HCl and extracted with ethyl acetate. The combined organic layers were washed sequentially with saturated NaHCO3, and brine, then dried (MgSO4) and concentrated. The resulting oil was purified by flash silica gel chromatography (6:4 ethyl ether-hexane) to yield 3-[3′,5′-bis(trifluoromethyl)phenyl]-1-propanol.

후처리

  1. temperaturewas maintained between −40° C. and −20° C
  2. stirringThe cloudy mixture was stirred overnight
  3. concentrationAfter concentrating in vacuo
  4. customthe residue was partitioned between ethyl acetate and water
  5. extractionextracted with ethyl acetate
  6. washThe combined organic layers were washed sequentially with saturated NaHCO3, and brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe resulting oil was purified by flash silica gel chromatography (6:4 ethyl ether-hexane)

출처 및 근거

ORD 기록
ord-a9c5c4d47c43400c88f9f64285575657
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07888364B2

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