Propargyl alcohol → ((Prop-2-yn-1-yloxy)methyl)benzene

HRID 2372100Notes

Reaction equation

[CH2:1](O)[C:2]#C.Cl[CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[CH2:8]([O:7][CH2:6][C:1]#[CH:2])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

Reactant 2

HCID 7859Propargyl alcohol

HCID 137983Benzyl chloromethyl ether

Product 1

HCID 6917484((Prop-2-yn-1-yloxy)methyl)benzene

Procedure

Propargyl alcohol is allowed to react with chloromethylbenzyl ether to obtain 1-benzyloxy-2-propyne (1). Then, this is allowed to react with Grignard reagent and a trifluoroacetic acid ester to obtain 5-benzyloxy-1,1,1-trifluoro-3-pentyne-2-one (2). Then, this is allowed to react with hydride of boron or aluminum to obtain 5-benzyloxy-1,1,1-trifluoro-3-pentyne-2-ol (3). This is acetylated or isobutylated and thereafter lipase or lipase-producing microorganism is allowed to act thereon to obtain optically active (R)-5-benzyloxy-1,1,1-trifluoro-3-pentyne-2-ol [(R)-(3)] and optically active (S)-5-benzyloxy-1,1,1-trifluoro-2-acetoxy (or butoxy)-3-pentyne [(S)-(4)].

Sources & evidence

ORD record: ord-043a8869186c475e9d0ac284475c6a2d
Source dataset: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05097075

Reaction notes

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