Dimethylformamide → HCID 22152297, 화합물

HRID 1111330노트

반응식

HRID 1111330 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:13])([CH3:12])[CH2:7][CH2:6]2.CN(C)[CH:16]=[O:17]>CCCCCC>[CH3:12][C:8]1([CH3:13])[C:9]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:11]([CH:16]=[O:17])[CH:10]=2)[CH2:6][CH2:7]1

참가 물질

4

반응물 2

HCID 6228DimethylformamideHCID 221522852,3-Dihydro-5-methoxy-1,1-dimethyl-1H-indene

생성물 1

HCID 22152297HCID 22152297, 화합물수율 40%

시약·촉매·용매 1

HCID 8058Hexane용매

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온도
100 °C

실험 절차

To a mixture of 10.60 g (60.0 mmol) of 5-methoxy-1,1-dimethylindane (see U.K. Patent Application No. GB 2,067,195 A for a method of obtaining this compound) and 6.5 g (90.0 mmol) of dimethylformamide was added 11.5 g (75.0 mmol) of phosphorous oxytrichloride. The mixture was heated at 100° C. for 5 h. The reaction mixture was cooled to ambient temperature and poured onto 100 g of ice. The aqueous residue was extracted with ether. The organic phase was washed with saturated sodium bicarbonate solution, dried and evaporated. The residue was chromatographed on silica gel (70 g) using a gradient from hexane to 2:98 (v/v) ether:hexane as eluent, There was obtained 4.86 g (23.8 mmol, 40%) of 1,1-dimethyl-5-methoxyindan-6-carboxaldehyde as a white solid after crystallization from hexane mp 51°-52° C.

후처리

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. extractionThe aqueous residue was extracted with ether
  3. washThe organic phase was washed with saturated sodium bicarbonate solution
  4. customdried
  5. customevaporated
  6. customThe residue was chromatographed on silica gel (70 g)

출처 및 근거

ORD 기록
ord-ff500adc42bf472cbc712eddebb9f8bb
출처 데이터셋
uspto-grants-1990_12
특허 번호
US04980352

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