Water → HCID 86650297、化合物

HRID 709443ノート

反応式

HRID 709443 の反応式
[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][S:14]C(=O)C)=[CH:8][CH:7]=1)(=[O:4])=[O:3].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[SH:14][CH2:13][CH2:12][C:9]1[CH:8]=[CH:7][C:6]([O:5][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:11][CH:10]=1

参加物

6

反応物 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride2 回HCID 86650296S-[2-[4-[(Methylsulfonyl)oxy]phenyl]ethyl] ethanethioate

生成物 1

HCID 86650297HCID 86650297、化合物収率 109.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
50 °C

実験手順

Thioacetic acid S-[2-(4-methanesulfonyloxy-phenyl)-ethyl]ester (250 mg, 0.91 mmol) was dissolved in anhydrous THF (2.5 mL) and LiAlH4 (38 mg, 1.0 mmol) was added in portions. After completed addition the mixture was warmed up to 50° C. and stirred for 1.5 h. The mixture was cooled down to 0° C. and excess LiAlH4 was hydrolyzed by the addition of H2O (0.8 mL), 2N aq. NaOH (1.0 mL) and THF (10 mL). Afterwards the reaction mixture was refluxed for 30 min then the precipitated salts were filtered off and the remaining filtrated was diluted with EtOAc. After extraction with brine and drying over Na2SO4, the solvent was evaporated under reduced pressure to afford the crude product as an oil (232 mg, 94.9%). 1H NMR (400 MHz, CDCl3): δ 7.29-7.31 (d, 2H), 7.21-7.23 (d, 2H), 3.31 (s, 3H), 2.81-2.85 (m, 2H), 2.68-2.73 (m, 2H).

後処理

  1. additionaddition the mixture
  2. temperatureThe mixture was cooled down to 0° C.
  3. temperatureAfterwards the reaction mixture was refluxed for 30 min
  4. filtrationthe precipitated salts were filtered off
  5. filtrationthe remaining filtrated
  6. additionwas diluted with EtOAc
  7. extractionAfter extraction with brine
  8. dry with materialdrying over Na2SO4
  9. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-3c156851c8314863b00584dfdb2fb955
出典データセット
uspto-grants-2015_11
特許番号
US09181181B2

反応ノート

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