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

HRID 466171ノート

反応式

HRID 466171 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a50e873b061b4749954183133f982adf
出典データセット
uspto-grants-1992_10
特許番号
US05155130

反応ノート

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