Propargyl alcohol → HCID 57789225, compound

HRID 1625548Notes

Reaction equation

HRID 1625548 reaction equation
[O:1]1[C@@H:5]2[CH2:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C@@H:4]2[NH:3][S:2]1(=[O:14])=[O:13].[CH2:15](O)[C:16]#[CH:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(/C(OC(C)C)=O)=N\C(OC(C)C)=O>CN(C)C=O>[CH2:17]([N:3]1[C@H:4]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[CH2:6][C@H:5]2[O:1][S:2]1(=[O:13])=[O:14])[C:16]#[CH:15]

Participants

6

Reactant 4

HCID 7859Propargyl alcoholHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 57789269HCID 57789269, compound

Product 1

HCID 57789225HCID 57789225, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2.2 g (10.4 mmol) 8a in 120 ml dimethylformamide was added 1.35 ml (22.8 mmol) prop-2-yn-1-ol and 6 g (22.8 mmol) triphenylphosphin and 4.42 ml (22.8 mmol) dipropan-2-yl (E)-diazene-1,2-dicarboxylate. The reaction mixture was stirred for 2 h and concentrated. The residue was purified by two subsequent column chromatographies (ethyl acetate hexane1:20→2:1) to obtain 970 mg (37%) of the desired product 8b.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by two subsequent column chromatographies (ethyl acetate hexane1:20→2:1)

Sources & evidence

ORD record
ord-aa1c50f3919d46cfaf652dea16cdb9d3
Source dataset
uspto-grants-2014_07
Patent number
US08784775B2

Reaction notes

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