Methane, dichloromethoxy- → 7-Fluoro-2,3-dihydrobenzo[b][1,4]dioxine-6-carbaldehyde

HRID 1271690ノート

反応式

HRID 1271690 の反応式
[F:1][C:2]1[CH:11]=[CH:10][C:5]2[O:6][CH2:7][CH2:8][O:9][C:4]=2[CH:3]=1.NC1C=C[C:16]2[O:17]CCOC=2C=1.COC(Cl)Cl>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[F:1][C:2]1[C:11]([CH:16]=[O:17])=[CH:10][C:5]2[O:6][CH2:7][CH2:8][O:9][C:4]=2[CH:3]=1

参加物

6

反応物 3

HCID 21004Methane, dichloromethoxy-HCID 891481,4-Benzodioxan-6-ylamineHCID 124645456-Fluoro-2,3-dihydro-1,4-benzodioxine

生成物 1

HCID 146448837-Fluoro-2,3-dihydrobenzo[b][1,4]dioxine-6-carbaldehyde

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 6-fluoro-2,3-dihydro-benzo[1,4]dioxine (prepared from 6-amino-2,3-dihydro-benzo[1,4]dioxine according to the procedure of V. Daukas, P. Gaidelis, R. Martinkus, S. Urboniene, Chemija, 1999, 10 (1), 59), (154 mg, 1 mmol) in dichloromethane (0.5 ml) was treated with dichloromethyl methyl ether (0.25 ml) at 0° C. under argon. Titanium tetrachloride (0.45 ml) in dichloromethane (0.5 ml) was added over 0.25 hours. The cooling bath was removed and the mixture was stirred at ambient temperature for 1 hour before being quenched with water and extracted with ether. The ether extract was washed with aqueous sodium bicarbonate and brine. Drying and evaporation afforded a brown oil which was purified by chromatography on silica (ethyl acetate/hexane) affording a clear oil (0.12 g).

後処理

  1. customThe cooling bath was removed
  2. custombefore being quenched with water
  3. extractionextracted with ether
  4. extractionThe ether extract
  5. washwas washed with aqueous sodium bicarbonate and brine
  6. customDrying
  7. customevaporation
  8. customafforded a brown oil which
  9. customwas purified by chromatography on silica (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-68e80ed2664c4d6487f1f1d84dcaf99e
出典データセット
uspto-grants-2007_04
特許番号
US07205408B2

反応ノート

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