1-(4-Phenylsulfonylphenyl)-3-hydroxy-3-methyl-4,4,4-trifluorobut-1-yne → 4,4,4-Trifluoro-3-hydroxy-3-methyl-1-(4-phenylsulfonylphenyl)-trans-but-1-ene

HRID 35884ノート

反応式

HRID 35884 の反応式
[H-].COCCO[Al+]OCCOC.[Na+].[H-].[C:15]1([S:21]([C:24]2[CH:29]=[CH:28][C:27]([C:30]#[C:31][C:32]([OH:38])([CH3:37])[C:33]([F:36])([F:35])[F:34])=[CH:26][CH:25]=2)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(OCC)C>[F:36][C:33]([F:34])([F:35])[C:32]([OH:38])([CH3:37])/[CH:31]=[CH:30]/[C:27]1[CH:26]=[CH:25][C:24]([S:21]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)(=[O:23])=[O:22])=[CH:29][CH:28]=1

参加物

4

反応物 2

HCID 199393031-(4-Phenylsulfonylphenyl)-3-hydroxy-3-methyl-4,4,4-trifluorobut-1-yneHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

生成物 1

HCID 98635074,4,4-Trifluoro-3-hydroxy-3-methyl-1-(4-phenylsulfonylphenyl)-trans-but-1-ene収率 79%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

To a solution of sodium bis(2-methoxyethoxy)aluminum hydride (1.5 mL, 3.4M in toluene) in freshly distilled diethyl ether (6 mL) was added a solution of 1-(4-phenylsulfonylphenyl)-3-hydroxy-3-methyl-4,4,4-trifluorobut-1-yne in diethyl ether (6 mL) dropwise. The rate of addition was controlled so that the reaction temperature did not exceed 8° C. The mixture was stirred for 15 minutes and was quenched at 0° C. with 3N sulfuric acid (15 mL). Water (10 mL) was added and the product was extracted into diethyl ether. The combined organic extracts were washed (brine) and dried. The solvent was evaporated and the material was purified by chromatography, with chloroform:diethyl ether (25:1) as the eluent, to give the title compound (848 mg, 79%).

後処理

  1. additionThe rate of addition
  2. customdid not exceed 8° C
  3. customwas quenched at 0° C. with 3N sulfuric acid (15 mL)
  4. additionWater (10 mL) was added
  5. extractionthe product was extracted into diethyl ether
  6. washThe combined organic extracts were washed (brine)
  7. customdried
  8. customThe solvent was evaporated
  9. customthe material was purified by chromatography, with chloroform:diethyl ether (25:1) as the eluent

出典と根拠

ORDレコード
ord-3e72d68742ee4716988a5c53520c7d6c
出典データセット
uspto-grants-1995_05
特許番号
US05411973

反応ノート

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