Hydrochloric Acid → 2-Chloro-1-(oxolan-3-yl)ethanone

HRID 612289

반응식

HRID 612289 반응식
[O:1]1[CH2:5][CH2:4][CH:3]([C:6]([OH:8])=O)[CH2:2]1.C(Cl)(=O)[C:10]([Cl:12])=O.[N+](=C)=[N-].Cl>ClCCl.CCOCC>[Cl:12][CH2:10][C:6]([CH:3]1[CH2:4][CH2:5][O:1][CH2:2]1)=[O:8]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 9550DiazomethaneHCID 65578Oxalyl chlorideHCID 4661317(R)-Tetrahydro-3-furoic acid

생성물 1

HCID 187800522-Chloro-1-(oxolan-3-yl)ethanone수율 88.1%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매2회

실험 절차

(RS)-3-Tetrahydrofuroic acid (3.48 g) in dichloromethane (40 ml) was treated with oxalyl chloride (11.43 g) as described in Example 1 (a). The resultant acid chloride in dichloromethane (40 ml) was then treated with excess diazomethane (60 mM) in ether (100 ml), followed by hydrogen chloride. The solution was washed once with brine, dried and concentrated. Flash chromatography on silica gel, eluting with 40% ethyl acetate/hexane afforded the title compound as a pale yellow oil, (3.924 g, 88%); νmax (CH2Cl2) 1735 and 1716 cm-1 ; 2.17 (2 H, dt, J 7.0, 7.5 Hz), 3.47-3.58 (1 H, m), 3.77-4.04 (4 H, m) and 4.18 (2 H, s); [mass spectrum: +ve ion (ammonia) MNH4+ (166)].

후처리

  1. washThe solution was washed once with brine
  2. customdried
  3. concentrationconcentrated
  4. washFlash chromatography on silica gel, eluting with 40% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-634359ccd1bc4432931a4a87e6b7c64b
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06001997

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