Sodium borohydride → 4-[2-Cyano-2-(4-trifluoromethoxyphenyl)ethyl]benzoic acid methyl ester

HRID 1816182노트

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HRID 1816182 반응식
[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[C:11]([C:23]#[N:24])[C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1.[BH4-].[Na+]>C1COCC1>[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([C:23]#[N:24])[C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]([F:20])([F:22])[F:21])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 674834364-[2-Cyano-2-(4-trifluoromethoxyphenyl)vinyl]benzoic acid methyl ester

생성물 1

HCID 426370344-[2-Cyano-2-(4-trifluoromethoxyphenyl)ethyl]benzoic acid methyl ester수율 97.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-20 °C

실험 절차

A solution of 4-[2-cyano-2-(4-trifluoromethoxyphenyl)vinyl]benzoic acid methyl ester (9.0 g, 25.92 mmol) in THF (50 mL) was stirred and cooled to −20° C. A solution of sodium borohydride in THF (100 mL) was added during 20 minutes. The cooling bath was removed and the mixture was stirred for two hours at room temperature and then kept at 5° C. for 16 hours. Ice (100 g) was added and the mixture was neutralised (pH 4-5) with 1 M hydrochloric acid (50 mL). The resulting mixture was extracted with DCM and washed with brine. The organic phase was dried (MgSO4), purified (Norite A), filtered and evaporated. The residue was dried at 40° C. in vacuo to afford 8.8 g (97%) of 4-[2-cyano-2-(4-trifluoromethoxyphenyl)ethyl]benzoic acid methyl ester.

후처리

  1. customThe cooling bath was removed
  2. waitkept at 5° C. for 16 hours
  3. additionIce (100 g) was added
  4. extractionThe resulting mixture was extracted with DCM
  5. washwashed with brine
  6. dry with materialThe organic phase was dried (MgSO4)
  7. custompurified (Norite A),
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was dried at 40° C. in vacuo

출처 및 근거

ORD 기록
ord-f396a276b43d4798b555a2c6bb4de2dc
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06881746B2

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