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

HRID 1271690노트

반응식

HRID 1271690 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-68e80ed2664c4d6487f1f1d84dcaf99e
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07205408B2

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