Water → (Z)-5-Fluoro-3-(2-hydroxyethyl)-2-methyl-1-(4-methylthiobenzylidene)indene

HRID 2371479노트

반응식

HRID 2371479 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)/[C:6]([CH3:20])=[C:5]2[CH2:21][C:22](O)=[O:23].B.O>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)/[C:6]([CH3:20])=[C:5]2[CH2:21][CH2:22][OH:23]

참가 물질

5

반응물 3

HCID 962WaterHCID 6331Borane2회HCID 5352624Sulindac Sulfide

생성물 1

HCID 70229088(Z)-5-Fluoro-3-(2-hydroxyethyl)-2-methyl-1-(4-methylthiobenzylidene)indene수율 76.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of (Z)-5-fluoro-2-methyl-1-(4-methylthiobenzylidene)inden-3-ylacetic acid, (1.70 g, 5 mmol) in THF (25 mL) at 0° C. and under nitrogen atmosphere, there was added a solution of borane (1M) in THF (5.5 mL, 5.5 mmol) and the mixture stirred in the cold for 30 minutes, then at room temperature for 2 hours. More borane was added (2.5 mL) and stirring was continued for 1 hour. Water was added slowly (20 mL), the THF was evaporated away and the residue partitioned between water and ethyl acetate. The crude product from the organic phase was purified by chromatography on silica gel using a 1:2 mixture of ethyl acetate-hexane as eluent to afford the desired product (1.25 g) as a yellow oil which solidified on standing. This was triturated with hexane and filtered to yield the title compound as a yellow solid, mp 101°-103° C.

후처리

  1. waitat room temperature for 2 hours
  2. stirringstirring
  3. waitwas continued for 1 hour
  4. customthe THF was evaporated away
  5. customthe residue partitioned between water and ethyl acetate
  6. customThe crude product from the organic phase was purified by chromatography on silica gel using
  7. additiona 1:2 mixture of ethyl acetate-hexane as eluent

출처 및 근거

ORD 기록
ord-55d2832184a54cdda3861695c1a2673a
출처 데이터셋
uspto-grants-1992_03
특허 번호
US05093356

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