tert-Butanol → HCID 20063323, 화합물

HRID 1084453노트

반응식

HRID 1084453 반응식
[CH3:1][CH:2]([CH3:14])[C:3]([C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])=[O:4].C(O)(C)(C)C.CC(C)([O-])C.[K+].Br[CH:27]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:28]([O:30][CH2:31][CH3:32])=[O:29]>C(O)C>[CH2:31]([O:30][C:28]([C:27]1([C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:3]([OH:4])([CH:2]([CH3:1])[CH3:14])[C:5]2[C:6](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:7](=[O:8])[O:9]1)=[O:29])[CH3:32]

참가 물질

6

반응물 4

HCID 6386tert-ButanolHCID 69637Diethyl bromomalonateHCID 3167392-(2-methylpropanoyl)benzoic acidHCID 23665647Potassium tert-butoxide

생성물 1

HCID 20063323HCID 20063323, 화합물수율 94.2%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A stirred mixture of 2-(2-methylpropanoyl)benzoic acid (44.27 g) and tert-butanol (300 ml) was treated portionwise with potassium tert-butoxide (28.14 g) over 5 minutes at room temperature and the reaction mixture stirred for a further 10 minutes and then treated dropwise over 10 minutes with a solution of diethyl bromomalonate (55.1 g) in ethanol (200 ml). The stirred mixture was refluxed for 18 hours and then evaporated to dryness. The residue was treated with diethyl ether (400 ml) and washed with water (400 ml). The aqueous phase was re-extracted with diethyl ether (200 ml) and the combined ethereal extracts washed with water (200 ml), saturated aqueous sodium hydrogen carbonate solution (200 ml) and water (200 ml), dried over magnesium sulphate and evaporated to give crude 3,3-bis(ethoxycarbonyl)-4-hydroxy-4-isopropyl-3,4-dihydroisocoumarin (76 g) as an amber oil.

후처리

  1. temperatureThe stirred mixture was refluxed for 18 hours
  2. customevaporated to dryness
  3. additionThe residue was treated with diethyl ether (400 ml)
  4. washwashed with water (400 ml)
  5. extractionThe aqueous phase was re-extracted with diethyl ether (200 ml)
  6. washthe combined ethereal extracts washed with water (200 ml), saturated aqueous sodium hydrogen carbonate solution (200 ml) and water (200 ml)
  7. dry with materialdried over magnesium sulphate
  8. customevaporated

출처 및 근거

ORD 기록
ord-fcc87bbbdb96499681acd2431c0a0fcd
출처 데이터셋
uspto-grants-1991_04
특허 번호
US05004747

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