Trityl chloride → 4-Trityloxy-but-2-en-1-ol

HRID 908505

반응식

HRID 908505 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.CCN(CC)CC.[CH2:28]([OH:33])/[CH:29]=[CH:30]\[CH2:31][OH:32].CCCCCC>CN(C1C=CN=CC=1)C.C(Cl)Cl.O>[C:1]([O:32][CH2:31][CH:30]=[CH:29][CH2:28][OH:33])([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

8

반응물 4

HCID 6456Trityl chloride2회HCID 8058HexaneHCID 8471TriethylamineHCID 6437902-Butene-1,4-diol, (2Z)-

생성물 1

HCID 541104114-Trityloxy-but-2-en-1-ol수율 85.2%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

Trityl chloride (557 mg; 2 mmol) Et3N (0.306 ml; 2.2 mmol) and DMAP (10 mg; 0.08 mmol) were added to an emulsion of cis-2-buten-1,4-diol (1.76 g; 20 mmol) in DCM (10 ml). The mixture was stirred at room temperature under atmosphere of nitrogen for 24 hours. After such period of time the complete disappearance of trityl chloride was observed by TLC (EtOAC/Hexane 50:50). DCM (20 ml) and water (10 ml) were added to the mixture. The phases were separated and the organic layer was washed with water (10 ml) and brine (10 ml). The solvent was dried over MgSO4 and evaporated under reduced pressure affording a residue (white oil) which was purified by flash chromatography using Hexane/EtOAc 70:30→40:60 as gradient which gave the title product as a colourless oil (563 mg, 81%).

후처리

  1. customThe phases were separated
  2. washthe organic layer was washed with water (10 ml) and brine (10 ml)
  3. dry with materialThe solvent was dried over MgSO4
  4. customevaporated under reduced pressure
  5. customaffording a residue (white oil) which
  6. customwas purified by flash chromatography

출처 및 근거

ORD 기록
ord-7ed79087e5734d59be9aaab4b8664e48
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017620B2

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