Hydrochloric Acid → Methyl 2-hydroxy-2-phenylpent-3-ynoate

HRID 358243

반응식

HRID 358243 반응식
[C:1]([Mg]Br)#[C:2][CH3:3].[Mg].C(Br)C.C#CC.[C:13]1([C:19](=[O:24])[C:20]([O:22][CH3:23])=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>CCOCC.C1COCC1>[C:13]1([C:19]([C:1]#[C:2][CH3:3])([OH:24])[C:20]([O:22][CH3:23])=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

9

반응물 6

HCID 313Hydrochloric AcidHCID 6332Ethyl BromideHCID 6335PropyneHCID 84835Methyl phenylglyoxalateHCID 5462224MagnesiumHCID 178419101HCID 178419101, 화합물

생성물 1

HCID 271980Methyl 2-hydroxy-2-phenylpent-3-ynoate

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

실험 절차

1-Propynylmagnesium bromide (0.2 mole) was made from magnesium (4.8 g., 0.2 g. atom) ethyl bromide (21.8 g., 0.2 mole) and excess propyne gas in 400 ml. of THF. The Grignard reagent then was siphoned under nitrogen into an addition funnel and added dropwise over a 40 minute period to a cooled solution of methyl phenylglyoxylate (32.8 g., 0.2 mole) in 200 ml. of THF. A slight temperature rise took place. The reaction mixture was stirred for 24 hours, and then poured onto a slurry of ice and 25 ml. conc. HCl. Ether was added, and the layers were separated. Several more ether extracts were made and the organic extracts combined and dried. The volatile components were stripped subsequently in vacuo and the residue distilled to yield 13.1 g. (32%) of the product, b.p. 109°-12° (0.2 mm.). The oil solidified on standing and melted at 64°-65° after recrystallization from 20°-40° petroleum ether.

후처리

  1. additionpoured onto a slurry of ice and 25 ml
  2. customthe layers were separated
  3. customdried
  4. distillationthe residue distilled
  5. customto yield 13.1 g
  6. custommelted at 64°-65° after recrystallization from 20°-40° petroleum ether

출처 및 근거

ORD 기록
ord-cddf046e23764c22ab1722be07cde170
출처 데이터셋
uspto-grants-1984_08
특허 번호
US04465834

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