Water → HCID 15097268, 화합물

HRID 974702노트

반응식

HRID 974702 반응식
[OH:1][CH2:2][CH:3]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH3:17])[CH2:4][OH:5].[H-].[Na+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CN(C)C=O>[CH2:20]([O:5][CH2:4][CH:3]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH3:17])[CH2:2][OH:1])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 15097267HCID 15097267, 화합물

생성물 1

HCID 15097268HCID 15097268, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

A solution of 3.06 g of 2-hydroxymethyl-7-(2-methoxyethoxy)methoxy-1-heptanol (prepared as described in Preparation 42) dissolved in 20 ml of dimethylformamide was added dropwise to 587 mg of sodium hydride (as a 55% dispersion in mineral oil) dispersed in 40 ml of dimethylformamide, whilst ice-cooling (at 5° to 7° C.). The mixture was then stirred at room temperature for 1 hour, after which 1.60 ml of benzyl bromide were added dropwise, whilst ice-cooling (at 5° to 7° C.). After stirring the reaction mixture at room temperature for 2 hours, it was poured into 300 ml of water and then extracted five times with ethyl acetate. The combined extracts were washed with water, dried and concentrated by evaporation under reduced pressure. The oily residue was subjected to column chromatography through 60 g of silica gel, and 2.37 g of the title compound were obtained from the fractions eluted with mixtures of hexane and ethyl acetate ranging from 2:1 to 1:1 by volume, as a colorless oil.

후처리

  1. temperaturecooling (at 5° to 7° C.)
  2. temperaturecooling (at 5° to 7° C.)
  3. stirringAfter stirring the reaction mixture at room temperature for 2 hours
  4. extractionextracted five times with ethyl acetate
  5. washThe combined extracts were washed with water
  6. customdried
  7. concentrationconcentrated by evaporation under reduced pressure

출처 및 근거

ORD 기록
ord-4b565ea633ae48fda297468bae60f95c
출처 데이터셋
uspto-grants-1991_11
특허 번호
US05068340

반응 노트

불러오는 중…