Methanol → 2,5-Dihydro-2,5-dimethoxy-2-(3-butynyl)furan

HRID 1032503노트

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HRID 1032503 반응식
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][C:8]#[CH:9].[C:10](=[O:13])([O-])[O-].[Na+].[Na+].BrBr.[CH3:18][OH:19]>>[CH3:18][O:19][C:2]1([CH2:6][CH2:7][C:8]#[CH:9])[CH:3]=[CH:4][CH:5]([O:13][CH3:10])[O:1]1

참가 물질

5

반응물 4

HCID 887Methanol2회HCID 10340Sodium CarbonateHCID 24408BromineHCID 221661432-(But-3-yn-1-yl)furan

생성물 1

HCID 147744262,5-Dihydro-2,5-dimethoxy-2-(3-butynyl)furan

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온도
25 °C

실험 절차

To a stirred mixture of 6.01 g of 4-(2-furyl)-1-butyne [Perfumery Essent. Oil Record., 57, 364 (1966)], 10.6 g of sodium carbonate and 150 ml of methanol at -25° C., was added dropwise a solution of 8.0 g of bromine in 50 ml of methanol during a period of 3 hours. The mixture was then stirred at 25° C. for 45 minutes and concentrated in vacuo. The residue was partitioned with ether and brine. The ether layer was separated, washed with brine, dried and concentrated. Distillation of the residue at 0.5mm gave 6.62 g of the desired compound as a light yellow liquid, bp 57°-61° C. (0.5 mm).

후처리

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned with ether and brine
  3. customThe ether layer was separated
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated
  7. distillationDistillation of the residue at 0.5mm

출처 및 근거

ORD 기록
ord-faaebcb1db3b402a8c26a27389d80a9d
출처 데이터셋
uspto-grants-1990_09
특허 번호
US04958037

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