Dimethylformamide → HCID 22152297、化合物

HRID 1111330ノート

反応式

HRID 1111330 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 22152297HCID 22152297、化合物収率 40%

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ff500adc42bf472cbc712eddebb9f8bb
出典データセット
uspto-grants-1990_12
特許番号
US04980352

反応ノート

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