Sodium Thiosulfate Pentahydrate → methyl 3-hydroxy-5-[(1S)-2-hydroxy-1-methylethoxy]benzoate

HRID 20524

反応式

HRID 20524 の反応式
C[Si](I)(C)C.[OH:6][C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([O:17][C@@H:18]([CH3:22])[CH2:19][O:20]C)[CH:16]=1)[C:10]([O:12][CH3:13])=[O:11].O.O.O.O.O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(#N)C.CO>[OH:6][C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([O:17][C@@H:18]([CH3:22])[CH2:19][OH:20])[CH:16]=1)[C:10]([O:12][CH3:13])=[O:11]

参加物

7

反応物 4

HCID 61475Sodium Thiosulfate PentahydrateHCID 85247Trimethylsilyl iodideHCID 516892Sodium BicarbonateHCID 59127146methyl 3-hydroxy-5-[(1S)-2-methoxy-1-methylethoxy]benzoate

生成物 1

HCID 59127187methyl 3-hydroxy-5-[(1S)-2-hydroxy-1-methylethoxy]benzoate収率 47%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6342Acetonitrile溶媒

実験手順

Trimethylsilyl iodide (115 mL, 0.79 mol) was added to a solution of methyl 3-hydroxy-5-[(1S)-2-methoxy-(1-methylethyl)oxy]benzoate (38.01 g, 0.158 mol) in acetonitrile (500 mL) and stirred for 24 hours. Methanol (300 mL) was added and the reaction stirred for 10 mins. 10% w/v Aqueous sodium thiosulfate pentahydrate (100 mL) was added to the mixture and stirred for 20 mins. The reaction mixture was neutralised with saturated aqueous sodium bicarbonate solution, the organic solvents removed in vacuo, and the product extracted into ethyl acetate (4×100 mL). The combined organic layers were dried (MgSO4), filtered and the solvents removed in vacuo. The crude material was crystallised from ethyl acetate to give the title compound (16.80 g)

後処理

  1. stirringthe reaction stirred for 10 mins
  2. additionwas added to the mixture
  3. stirringstirred for 20 mins
  4. customthe organic solvents removed in vacuo
  5. extractionthe product extracted into ethyl acetate (4×100 mL)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvents removed in vacuo
  9. customThe crude material was crystallised from ethyl acetate

出典と根拠

ORDレコード
ord-c13cbd53a2484403be1275b169a3f48d
出典データセット
uspto-grants-2010_06
特許番号
US07745475B2

関連ノート

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