Potassium Carbonate → tert-butyl 6-benzyloxy-2H-1-benzopyran-3-carboxylate

HRID 466171노트

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HRID 466171 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([OH:17])=[C:13]([CH:16]=1)[CH:14]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:24]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])(=[O:27])[CH:25]=[CH2:26]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:17][CH2:26][C:25]([C:24]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[CH:14][C:13]=2[CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 15458tert-Butyl acrylateHCID 8783625-(Benzyloxy)-2-hydroxybenzaldehyde

생성물 1

HCID 14971253tert-butyl 6-benzyloxy-2H-1-benzopyran-3-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

5-Benzyloxy-2-hydroxybenzaldehyde (2.01 g, 8.80 mmol) is dissolved in 30 ml of DMF and treated successively with potassium carbonate (1.22 g, 8.80 mmol) and tert-butyl acrylate (1.22 g, 13.2 mmol). The mixture is heated at 100° C. for 1 hour. The temperature is gradually raised to 135° C. over a period of 2 hours, and held at 135° C. for 1 hour. The resultant dark mixture is cooled and evaporated to remove most of DMF. The residue is partitioned between ether and water, and the aqueous phase is discarded. The organic layer is dried (MgSO4), evaporated and purified by silica gel chromatography (6% ethyl acetate/hexane) to give tert-butyl 6-benzyloxy-2H-1-benzopyran-3-carboxylate as a yellow crystalline solid, m.p. 64°-67° C.

후처리

  1. temperatureThe temperature is gradually raised to 135° C. over a period of 2 hours
  2. temperatureThe resultant dark mixture is cooled
  3. customevaporated
  4. customto remove most of DMF
  5. customThe residue is partitioned between ether and water
  6. dry with materialThe organic layer is dried (MgSO4)
  7. customevaporated
  8. custompurified by silica gel chromatography (6% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-a50e873b061b4749954183133f982adf
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05155130

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