Veratraldehyde → 2-[(3,4-Dimethoxyphenyl)methylidene]-1,3-dithiolane

HRID 620065노트

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HRID 620065 반응식
C(OP([CH:9]1[S:14][CH2:13][CH2:12]C[S:10]1)(OCC)=O)C.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH:20]=O.[OH-].[Na+]>ClCCl.[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[S:14]1[CH2:13][CH2:12][S:10][C:9]1=[CH:20][C:19]1[CH:22]=[CH:23][C:24]([O:25][CH3:26])=[C:17]([O:16][CH3:15])[CH:18]=1

참가 물질

6

반응물 3

HCID 8419VeratraldehydeHCID 14798Sodium HydroxideHCID 10869064Diethyl (1,3-Dithian-2-yl)phosphonate

생성물 1

HCID 230390002-[(3,4-Dimethoxyphenyl)methylidene]-1,3-dithiolane

시약·촉매·용매 2

HCID 66133Benzyl triethylammonium chloride촉매HCID 6344Dichloromethane용매2회

실험 절차

A solution of 2-diethoxyphosphoryl-1,3-dithiane (23.4 g) and 3,4-dimethoxybenzaldehyde (16.0 g) in dichloromethane (70 ml) is added to a mixture of dichloromethane (85 ml), a 50% aqueous solution of sodium hydroxide (170 ml) and triethylbenzylammonium chloride (1.4 g). The mixture is stirred for 24 hours at room temperature. The two phases are then separated. The aqueous solution is extracted with dichloromethane (100 ml) and the combined organic solutions are washed with a 10% aqueous solution of ammonium chloride (3×100 ml) and with water (2×100 ml). The dichloromethane is dried over magnesium sulphate and evaporated in vacuo. The residue is purified by column chromatography on silica gel using chloroform as eluant. The product is dried in vacuo to constant weight to yield (1,3-dithiolan-2-ylidene)-(3,4-dimethoxyphenyl)-methane, m.p. 74°-75°.

후처리

  1. customThe two phases are then separated
  2. extractionThe aqueous solution is extracted with dichloromethane (100 ml)
  3. washthe combined organic solutions are washed with a 10% aqueous solution of ammonium chloride (3×100 ml) and with water (2×100 ml)
  4. dry with materialThe dichloromethane is dried over magnesium sulphate
  5. customevaporated in vacuo
  6. customThe residue is purified by column chromatography on silica gel
  7. customThe product is dried in vacuo to constant weight

출처 및 근거

ORD 기록
ord-0f37c9248a30456a9319dc2d4ac67112
출처 데이터셋
uspto-grants-1989_04
특허 번호
US04818765

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