2-Cyclopropyl-7,8-dimethoxy-2H-chromene-5-carboxylic acid methyl ester → 2-Cyclopropyl-7,8-dimethoxy-2H-1-benzopyran-5-methanol

HRID 1367635노트

반응식

HRID 1367635 반응식
C[O:2][C:3]([C:5]1[C:6]2[CH:7]=[CH:8][CH:9]([CH:19]3[CH2:21][CH2:20]3)[O:10][C:11]=2[C:12]([O:17][CH3:18])=[C:13]([O:15][CH3:16])[CH:14]=1)=O.COCCO[AlH2-]OCCOC.[Na+]>O1CCCC1.CC(OC)(C)C>[CH:19]1([CH:9]2[CH:8]=[CH:7][C:6]3[C:11](=[C:12]([O:17][CH3:18])[C:13]([O:15][CH3:16])=[CH:14][C:5]=3[CH2:3][OH:2])[O:10]2)[CH2:20][CH2:21]1

참가 물질

5

반응물 2

HCID 116449742-Cyclopropyl-7,8-dimethoxy-2H-chromene-5-carboxylic acid methyl esterHCID 16684438Red-Al

생성물 1

HCID 115506842-Cyclopropyl-7,8-dimethoxy-2H-1-benzopyran-5-methanol수율 82.3%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 15413tert-Butyl methyl ether용매

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온도
40 °C

실험 절차

Methyl ester 2 (2 g, 6.2 mmol) was dissolved in 30 ml tetrahydrofurane and 2.7 ml of a 3.5-M solution of Red-Al (9.4 mmol) was added. The mixture was stirred at 40° C. for 3 hours. The solution was diluted with 100 ml of TBME and slowly quenched by addition of 50 ml of a 30% potassium-tartrate solution. The layers were separated and the organic solution was washed with brine (2 times 30 ml), dried over magnesium sulfate and concentrated. The pure alcohol 4 (1.34 g, 5.1 mmol) was obtained as a white-yellow solid.

후처리

  1. customslowly quenched by addition of 50 ml of a 30% potassium-tartrate solution
  2. customThe layers were separated
  3. washthe organic solution was washed with brine (2 times 30 ml)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-365dde01fbf14fa9bffb9d6163b257d4
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893262B2

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