Methane, dichloromethoxy- → 6-Fluorochroman-8-carbaldehyde

HRID 1738891ノート

反応式

HRID 1738891 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH2:6][CH2:5]2.[CH3:12][O:13]C(Cl)Cl>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH:12]=[O:13])[CH:11]=1)[O:8][CH2:7][CH2:6][CH2:5]2

参加物

5

反応物 2

HCID 21004Methane, dichloromethoxy-HCID 114691696-Fluoro-3,4-dihydro-2H-1-benzopyran

生成物 1

HCID 112291326-Fluorochroman-8-carbaldehyde収率 108.8%

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

13.74 g (90.28 mmol) of 6-fluorochroman are dissolved in 250 ml of methylene chloride. The whole is cooled to 0° C. and 20.15 ml (0.18 mol) of TiCl4 are added dropwise. The solution becomes brown and is stirred for 10 minutes at room temperature. 8.78 ml (99.3 mmol) of α,α-dichloromethyl ether are then introduced. The whole is stirred overnight at room temperature, poured into ice-cold water and decanted. The organic phase is dried and evaporated to yield 17.7 g of a residue which is purified by chromatography on silica (eluant CH2Cl2 /cyclohexane: 50/50). 6.3 g of the expected product are obtained. Yield: 38.7%.

後処理

  1. stirringThe whole is stirred overnight at room temperature
  2. additionpoured into ice-cold water
  3. customdecanted
  4. customThe organic phase is dried
  5. customevaporated

出典と根拠

ORDレコード
ord-186ac148afc24b12a2644dc07ed361cf
出典データセット
uspto-grants-1999_10
特許番号
US05965575

反応ノート

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