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

HRID 1009211노트

반응식

HRID 1009211 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

반응 조건

온도
40 °C

실험 절차

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.).

후처리

  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)

출처 및 근거

ORD 기록
ord-237e216f9c534e61a207f2d196d474de
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973072B2

반응 노트

불러오는 중…