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

HRID 379624ノート

反応式

HRID 379624 の反応式
[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]

参加物

5

反応物 3

HCID 962WaterHCID 6331Borane2 回HCID 5352624Sulindac Sulfide

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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 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.

後処理

  1. waitat room temperature for 2 hours
  2. stirringstirring
  3. waitwas continued for 1 hour
  4. customthe THF was evaporated
  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

出典と根拠

ORDレコード
ord-ecebc683b96b4588968f5db5ebc1e022
出典データセット
uspto-grants-2001_10
特許番号
US06300346B1

反応ノート

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