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

HRID 1421802

反応式

HRID 1421802 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

(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 (2H, dt, J 7.0, 7.5 Hz), 3.47-3.58 (1H, m), 3.77-4.04 (4H, m) and 4.18 (2H, s); [mass spectrum: +ve ion (ammonia) MNH4+ (166)].

後処理

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

出典と根拠

ORDレコード
ord-ffa0d5c1d0d14b168222072d325f8d52
出典データセット
uspto-grants-2000_06
特許番号
US06077952

関連ノート

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