Sodium hydride → [(R)-2-(2,2-diethoxyethoxy)-4-pentenyloxymethyl]benzene

HRID 538017

반응식

HRID 538017 반응식
[H-].[Na+].[CH2:3]([O:10][CH2:11][C@H:12]([OH:16])[CH2:13][CH:14]=[CH2:15])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:18][CH:19]([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22]>O1CCCC1>[CH2:21]([O:20][CH:19]([O:23][CH2:24][CH3:25])[CH2:18][O:16][C@H:12]([CH2:13][CH:14]=[CH2:15])[CH2:11][O:10][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:22]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 10375318(2R)-1-(benzyloxy)pent-4-en-2-ol

생성물 1

HCID 59281174[(R)-2-(2,2-diethoxyethoxy)-4-pentenyloxymethyl]benzene

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

This reaction was carried out in two identical experiments. To a 0° C. suspension of sodium hydride (60% in mineral oil, 125 g, 3.12 mol) in tetrahydrofuran (1 L) was added a solution of C1 (200 g, 1.04 mol) in tetrahydrofuran (500 mL). The reaction was stirred for 30 minutes at room temperature, whereupon 2-bromo-1,1-diethoxyethane (528 g, 2.68 mol) was added, and the reaction mixture was heated at reflux for 18 hours. The mixture was carefully quenched with water (2×300 mL) and the combined experiments were concentrated in vacuo. The aqueous residue was partitioned between ethyl acetate (5 L) and water (5 L). The organic layer was washed with saturated aqueous sodium chloride solution (5 L), dried, and concentrated. Purification via silica gel chromatography (Eluent: 20:1 petroleum ether/ethyl acetate) provided the product as a yellow oil. Yield: 300 g, 0.97 mol, 47%. 1H NMR (400 MHz, CDCl3) δ 7.26-7.37 (m, 5H), 5.78-5.90 (m, 1H), 5.01-5.13 (m, 2H), 4.61 (t, J=5.3 Hz, 1H), 4.55 (s, 2H), 3.48-3.74 (m, 9H), 2.30-2.36 (m, 2H), 1.22 (t, J=7.1 Hz, 3H), 1.21 (t, J=7.0 Hz, 3H).

후처리

  1. additionwas added
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for 18 hours
  4. customThe mixture was carefully quenched with water (2×300 mL)
  5. concentrationthe combined experiments were concentrated in vacuo
  6. customThe aqueous residue was partitioned between ethyl acetate (5 L) and water (5 L)
  7. washThe organic layer was washed with saturated aqueous sodium chloride solution (5 L)
  8. customdried
  9. concentrationconcentrated
  10. customPurification via silica gel chromatography (Eluent: 20:1 petroleum ether/ethyl acetate)

출처 및 근거

ORD 기록
ord-f45f430bf13b4db892b8a83150985fa2
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865706B2

연결된 노트

불러오는 중…