Acetic Acid → diethyl 6-acetyl-3,4-dihydro-8-propyl-7-hydroxy-2H-1-benzopyran-2,2-dipropanoate

HRID 2371652ノート

反応式

HRID 2371652 の反応式
[CH2:1]([C:4]1[C:13]2[O:12][C:11]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])([CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:10][CH2:9][C:8]=2[CH:7]=[CH:6][C:5]=1[OH:28])[CH2:2][CH3:3].[C:29](O)(=[O:31])[CH3:30]>[Cl-].[Zn+2].[Cl-]>[C:29]([C:6]1[C:5]([OH:28])=[C:4]([CH2:1][CH2:2][CH3:3])[C:13]2[O:12][C:11]([CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:10][CH2:9][C:8]=2[CH:7]=1)(=[O:31])[CH3:30]

参加物

4

反応物 2

HCID 176Acetic AcidHCID 15157486diethyl 3,4-dihydro-8-propyl-7-hydroxy-2H-1-benzopyran-2,2-dipropanoate

生成物 1

HCID 15157494diethyl 6-acetyl-3,4-dihydro-8-propyl-7-hydroxy-2H-1-benzopyran-2,2-dipropanoate

試薬・触媒・溶媒 1

HCID 3007855Zincchloride触媒

実験手順

To a solution of 790 mg (2.01 mmol) of the title product of Example 44 in 4 ml of acetic acid was added 547 mg (4.02 mmol) of anhydrous zinc chloride. The mixture was stirred for six hours at reflux, and then permitted to cool. The mixture was partitioned between ethyl acetate and dilute hydrochloric acid. The aqueous layer was further extracted with two portions of ethyl acetate. The combined organic extracts were washed successively with five portions of aqueous sodium bicarbonate, water, and then brine. The extracts were dried over sodium sulfate, filtered, and the solvent removed under reduced pressure. Chromatography of the residue over silica gel using 25% ethyl acetate/hexane as eluent gave the title compound, 230 mg.

後処理

  1. temperatureat reflux
  2. temperatureto cool
  3. customThe mixture was partitioned between ethyl acetate and dilute hydrochloric acid
  4. extractionThe aqueous layer was further extracted with two portions of ethyl acetate
  5. washThe combined organic extracts were washed successively with five portions of aqueous sodium bicarbonate, water
  6. dry with materialThe extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure

出典と根拠

ORDレコード
ord-843ce68f4a4c4bccb551b0af42613444
出典データセット
uspto-grants-1992_03
特許番号
US05093353

反応ノート

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