Diethyl Ether → 4-Hydroxy-4-methyl-7-oxo-1-octyne

HRID 126719

반응식

HRID 126719 반응식
[CH2:1]([Mg]Br)[C:2]#[CH:3].[Mg].C(Br)C#C.CO[CH2:13][CH2:14][C:15](=[O:17])[CH3:16].CC[O:20][CH2:21][CH3:22]>>[OH:20][C:21]([CH3:22])([CH2:13][CH2:14][C:15](=[O:17])[CH3:16])[CH2:3][C:2]#[CH:1]

참가 물질

6

반응물 5

HCID 3283Diethyl Ether2회HCID 7842Propargyl bromideHCID 1388892-Butanone, 4-methoxy-HCID 5462224MagnesiumHCID 178455849HCID 178455849, 화합물

생성물 1

HCID 202875984-Hydroxy-4-methyl-7-oxo-1-octyne

실험 절차

To a stirred solution of propargylmagnesium bromide in 35 ml. of ether, prepared from 7.65 g. (0.3 moles) of magnesium, 170 mg. of mercuric chloride and 33.6 g. (0.28 moles) of propargyl bromide, is added dropwise under argon atmosphere a solution of 25 g. (0.245 moles) of 4-methoxy-2-butanone [L. R. Fedor, J. Am. Chem. Soc., 91:4, 908 (1969)] in 20 ml. of ether at a rate to maintain gentle refluxing. The resulting mixture is stirred at ambient temperature for an additional 30 minutes then quenched at 5° C. by the addition of 140 ml. of saturated ammonium chloride solution. After filtration the ether phase is separated; the aqueous phase is extracted twice with additional ether. The combined ether extracts are washed with saturated sodium chloride solution, dried with anhydrous magnesium sulfate and taken to dryness in vacuo. Distillation of the residual oil provided 13.7 g. (40%) of product; b.p. 84°-85° C. (13 mm.).

후처리

  1. customthen quenched at 5° C. by the addition of 140 ml
  2. filtrationAfter filtration the ether phase
  3. customis separated
  4. extractionthe aqueous phase is extracted twice with additional ether
  5. washThe combined ether extracts are washed with saturated sodium chloride solution
  6. dry with materialdried with anhydrous magnesium sulfate
  7. distillationDistillation of the residual oil
  8. customprovided 13.7 g

출처 및 근거

ORD 기록
ord-5c760fdfd3744025a9b9928d2d4a4739
출처 데이터셋
uspto-grants-1981_03
특허 번호
US04254036

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