Dimethyl Carbonate → Methyl 4-oxooxane-3-carboxylate

HRID 713379노트

반응식

HRID 713379 반응식
[O:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.[CH3:8][O:9][C:10](=O)[O:11]C.CC(C)([O-])C.[K+]>>[CH3:8][O:9][C:10]([CH:3]1[C:4](=[O:7])[CH2:5][CH2:6][O:1][CH2:2]1)=[O:11]

참가 물질

4

반응물 3

HCID 12021Dimethyl CarbonateHCID 121599Tetrahydro-4H-pyran-4-one2회HCID 23665647Potassium tert-butoxide

생성물 1

HCID 14666555Methyl 4-oxooxane-3-carboxylate수율 26.5%

실험 절차

To a solution of tetrahydro-pyran-4-one (1.3 kg, 12.98 mol) and carbonic acid dimethyl ester (11.69 kg, 129.8 mol) was added solid potassium tert-butoxide (1.89 kg, 16.08 mol) in portions at −10° C. over 2 h under nitrogen protection. The suspension was stirred at room temperature 10 h after the addition. LCMS (215 nm) indicated that tetrahydro-pyran-4-one had been completely consumed. The reaction was acidified by HCl (2 N) to pH 6˜7 and then the phases were separated. The organic phase was washed with water (3 L×2) and the combined aqueous phases were extracted with MTBE (2.5 L×2). The combined organic phase was concentrated under reduced pressure at 25° C. to remove most of MTBE. The residue was distilled out by oil pump (˜200 Pa) at 74° C. to give the title compound as colorless oil (545 g, 26.3%). CHN analysis: calculated (results). C, 53.16 (53.10), H, 6.37 (6.245), N, 0.00 (0.00).

후처리

  1. additionafter the addition
  2. customhad been completely consumed
  3. customthe phases were separated
  4. washThe organic phase was washed with water (3 L×2)
  5. extractionthe combined aqueous phases were extracted with MTBE (2.5 L×2)
  6. concentrationThe combined organic phase was concentrated under reduced pressure at 25° C.
  7. customto remove most of MTBE
  8. distillationThe residue was distilled out by oil pump (˜200 Pa) at 74° C.

출처 및 근거

ORD 기록
ord-c7949e44dc8049629dbfdf2249bcfd03
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181266B2

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