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

HRID 908505

Reaction equation

HRID 908505 reaction equation
[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

Participants

8

Reactant 4

HCID 6456Trityl chloride2×HCID 8058HexaneHCID 8471TriethylamineHCID 6437902-Butene-1,4-diol, (2Z)-

Product 1

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

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-7ed79087e5734d59be9aaab4b8664e48
Source dataset
uspto-grants-2011_09
Patent number
US08017620B2

Linked notes

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