Acetic Acid → Uniconazole

HRID 2249019

반응식

HRID 2249019 반응식
C(O)(=O)C.C[C@H](N)[C@H](O)C1C=CC=CC=1.Cl.[BH4-].[Na+].[Cl:19][C:20]1[CH:25]=[CH:24][C:23](/[CH:26]=[C:27](/[N:34]2[CH:38]=[N:37][CH:36]=[N:35]2)\[C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:22][CH:21]=1.Cl>ClC1C=CC=CC=1.CN(C)C=O.O>[Cl:19][C:20]1[CH:25]=[CH:24][C:23](/[CH:26]=[C:27](/[N:34]2[CH:38]=[N:37][CH:36]=[N:35]2)\[CH:28]([OH:33])[C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:22][CH:21]=1

참가 물질

9

반응물 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 62943Phenylpropanolamine HydrochlorideHCID 4311764Sodium borohydrideHCID 10913254(E)-1-(4-chlorophenyl)-2-(1,2,4-triazol-1-yl)-4,4-dimethyl-1-penten-3-one

생성물 1

HCID 6436604Uniconazole수율 96%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 7964Chlorobenzene용매2회

실험 절차

In a nitrogen atmosphere, 0.393 g (0.0065 mole) of acetic acid was added to a suspension of 8.18 g (0.0436 mole) of (-)-norephedrine hydrochloride in 62.17 g of chlorobenzene, and then a solution of 1.815 g (0.0480 mole) of sodium borohydride in 9.35 g of dimethylformamide was added dropwise to this suspension at 5° to 10° C. for 1.5 hours. Thereafter, the resulting mixture was stirred at room temperature for 1 hour, and then a solution of 8.42 g (0.0291 mole; E/Z=99.8/0.2) of (E)-1-(4-chlorophenyl)-2-(1,2,4-triazol-1-yl)-4,4-dimethyl-1-penten-3-one in 49.7 g of chlorobenzene was added at room temperature. The resulting mixture was stirred at the same temperature for 18 hours. The reaction solution was decomposed with addition of 17.50 g of 10% hydrochloric acid and 5 g of water, and the organic layer was separated, washed with water and concentrated under reduced pressure to obtain 8.15 g (+)-(E)-1-(4-chlorophenyl)-2-(1,2,4-triazol-1-yl)-4,4-dimethyl-1-penten-3-ol as a crystal. The conversion was 99.8%, and the composition of the product obtained was: E-form alcohol, 90.8%; saturated alcohol, 2.3%; and Z-form alcohol, 6.9%. The enantiomer ratio of the E-form alcohol was: (+)-isomer, 81.0% and (-)-isomer, 19.0%. The optical yield was 62.0%.

후처리

  1. stirringThe resulting mixture was stirred at the same temperature for 18 hours
  2. customthe organic layer was separated
  3. washwashed with water
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-f80e51ff994c46d6b20bdad93123b7fe
출처 데이터셋
uspto-grants-1991_08
특허 번호
US05041651

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