Hydrochloric Acid → (2R)-2-(1-hydroxy-1-(3-methoxyphenyl)methyl]cyclohexanone

HRID 377321

반응식

HRID 377321 반응식
C[O:2][C:3]1[CH:20]=[CH:19][CH:18]=[C:17](OC)[C:4]=1C([C@@]([C@H](C(O)=O)O)(O)C(O)=O)=O.C[Si](C)(C)OC1CCCCC=1.[CH3:34][O:35][C:36]1[CH:37]=[C:38]([CH:41]=[CH:42][CH:43]=1)[CH:39]=[O:40].Cl>C(#N)CC.O1CCCC1>[OH:40][CH:39]([C@H:4]1[CH2:17][CH2:18][CH2:19][CH2:20][C:3]1=[O:2])[C:38]1[CH:41]=[CH:42][CH:43]=[C:36]([O:35][CH3:34])[CH:37]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 115693-MethoxybenzaldehydeHCID 81161Cyclohexene, 1-((trimethylsilyl)oxy)-HCID 70267832(R,R)-mono(2,6-dimethoxybenzoyl)tartaric acid

생성물 1

HCID 70265867(2R)-2-(1-hydroxy-1-(3-methoxyphenyl)methyl]cyclohexanone수율 149.5%

시약·촉매·용매 2

HCID 7854Propionitrile용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To a solution of (R,R)-mono(2,6-dimethoxybenzoyl)tartaric acid (314 mg) in propionitrile (5 ml) was added 1M BH3 solution (1.0 ml) in tetrahydrofuran at 0° C. under N2. The reaction mixture was stirred for 1 hour at 0° C., and then the solution was cooled to -78° C. To this were added 1-(trimethylsilyl-oxy)cyclohexene (1.0 g) and 3-methoxybenzaldehyde (680 mg) successively. After stirring for 2 hours, the solution was poured into 1N-hydrochloric acid and the product was extracted with ether. The solvent was evaporated, and the residue was treated with 1N-hydrochloric acid-tetrahydrofuran solution (2 ml, 1:1). Usual chromatographic separation gave (2R)-2-(1-hydroxy-1-(3-methoxyphenyl)methyl]cyclohexanone (350 mg).

후처리

  1. temperaturethe solution was cooled to -78° C
  2. stirringAfter stirring for 2 hours
  3. extractionthe product was extracted with ether
  4. customThe solvent was evaporated
  5. additionthe residue was treated with 1N-hydrochloric acid-tetrahydrofuran solution (2 ml, 1:1)
  6. customUsual chromatographic separation

출처 및 근거

ORD 기록
ord-2cf3118a80684934bb0069fd596a3ca9
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06025375

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