Water → HCID 10882092, 화합물

HRID 908511

반응식

HRID 908511 반응식
[C:1](Cl)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]([OH:26])/[CH:22]=[CH:23]/[CH2:24][OH:25].CCCCCC.CCOC(C)=O.O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]([O:25][CH2:24]/[CH:23]=[CH:22]/[CH2:21][OH:26])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 6456Trityl chloride3회HCID 175854trans-2-Butene-1,4-diolHCID 21226206Ethyl acetate hexane

생성물 1

HCID 10882092HCID 10882092, 화합물

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매2회HCID 6344Dichloromethane용매2회

실험 절차

A solution of Trityl chloride (500 mg; 1.81 mmol), TEA (0.277 ml; 1.99 mmol) and DMAP (8.8 mg; 0.072 mmol) in dry DCM (5 ml) was added with a syringe to a solution of the diol (10) (800 mg; 9.07 mmol) in DCM (15 ml). The mixture was stirred at room temperature for 1 hour and 30 minutes, then other TrCl, TEA and DMAP (half quantities than before) were added. The reaction was stirred at the same temperature until TLC (Hexane/EtOAc 50:50) showed complete disappearance of Trityl chloride. After 1.5 hours water (20 ml) was added and the reaction was stirred for few minutes, then the phases were separated. The organic layer was washed with water (25 ml) and brine (25 ml). The solvent was dried over MgSO4 and evaporated to afford a crude oil which was purified by flash chromatography using Hexane/EtOAc 50:50 as eluent which gave the title compound as a colourless oil, 637 mg, 71%. Rf: 0.72 in Hexane/EtOAc 50:50 (UV/PMA).

후처리

  1. stirringthe reaction was stirred for few minutes
  2. customthe phases were separated
  3. washThe organic layer was washed with water (25 ml) and brine (25 ml)
  4. dry with materialThe solvent was dried over MgSO4
  5. customevaporated
  6. customto afford a crude oil which
  7. customwas purified by flash chromatography

출처 및 근거

ORD 기록
ord-b8e3d0c9634b4405b21b1edb62d11ce5
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017620B2

연결된 노트

불러오는 중…