Formaldehyde → 3,3-Bis(hydroxymethyl)-2,3-dihydro-4H-1-benzothiopyran-4-one

HRID 1009211ノート

反応式

HRID 1009211 の反応式
[S:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH2:3][CH2:2]1.[CH2:12]=[O:13].[C:14](=[O:17])([O-])[O-].[K+].[K+]>CO.O>[OH:13][CH2:12][C:3]1([CH2:14][OH:17])[C:4](=[O:11])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[S:1][CH2:2]1

参加物

6

反応物 3

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 19048Thiochroman-4-one

生成物 1

HCID 27640233,3-Bis(hydroxymethyl)-2,3-dihydro-4H-1-benzothiopyran-4-one

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
40 °C

実験手順

A solution of thiochroman-4-one (2.0 g, 12 mmol) in MeOH (40 ml) and water (8 ml) was admixed with 35% eq. formalin solution (8 ml) and potassium carbonate (200 mg). The reaction mixture was stirred at 40° C. for 2 h and then at RT for 2 h, the solvent was removed under reduced pressure and the residue was admixed with water. The aqueous solution was extracted repeatedly with EtOAc, the combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. After column chromatography purification of the residue (silica gel, 1:1 cyclohexane/EtOAc), the desired product was obtained as a white solid (1.71 g, 63% of theory, m.p. 136-139° C.).

後処理

  1. waitat RT for 2 h
  2. customthe solvent was removed under reduced pressure
  3. extractionThe aqueous solution was extracted repeatedly with EtOAc
  4. dry with materialthe combined organic phases were dried over sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customAfter column chromatography purification of the residue (silica gel, 1:1 cyclohexane/EtOAc)

出典と根拠

ORDレコード
ord-237e216f9c534e61a207f2d196d474de
出典データセット
uspto-grants-2011_07
特許番号
US07973072B2

反応ノート

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