Propargyl bromide → 4-Hydroxy-4-methyl-7-oxa-1-octyne

HRID 848909

반응식

HRID 848909 반응식
[CH2:1]([Mg]Br)[C:2]#C.[Mg].[CH2:7](Br)C#C.[CH3:11][O:12][CH2:13][CH2:14][C:15](=[O:17])[CH3:16]>CCOCC>[OH:17][C:15]([CH3:7])([CH2:14][CH2:13][O:12][CH3:11])[CH2:16][C:1]#[CH:2]

참가 물질

6

반응물 4

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

생성물 1

HCID 127862294-Hydroxy-4-methyl-7-oxa-1-octyne

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

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-94de3cf87cb64ef48b91e77c406ba337
출처 데이터셋
uspto-grants-1981_10
특허 번호
US04297516

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