2-Butyn-1-ol → HCID 70083899, compound

HRID 2417272Notes

Reaction equation

HRID 2417272 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH:5]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=1)[S:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:2].[CH2:22](O)[C:23]#[C:24][CH3:25].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC>C1COCC1>[CH2:1]([O:3][C:4](=[O:21])[CH:5]([S:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:22][C:23]#[C:24][CH3:25])=[CH:11][CH:12]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=1)[CH3:2]

Participants

6

Reactant 4

HCID 129912-Butyn-1-olHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 131724674Ethyl(3-chlorophenyl)[(4-hydroxyphenyl)sulfanyl]acetate

Product 1

HCID 70083899HCID 70083899, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The ethyl(3-chlorophenyl)[(4-hydroxyphenyl)sulfanyl]acetate (4.2 g, 13 mmol) was stirred with THF (100 ml) in a dried two-necked flask under inert conditions. The 2-butyn-1-ol (0.97 ml, 13 mmol) and 1,1′(azodicarbonyl)dipiperidine (3.94 g, 15.6 mmol). Tributylphosphine (3.90 ml, 15.6 mmol) was added dropwise at 0° C. The reaction mixture was allowed to stir at room temperature under nitrogen for 2 hours before it was concentrated. The residue was triturated with ether and the filtrate was concentrated, Ethyl{[4-(2-butynyloxy)phenyl]sulfanyl}(3-chlorophenyl)acetate was isolated as a yellow oil (4.08 g) after silica-gel column chromatography, using methylene chloride as the mobile phase. Yield 84%; MS(EI): 375 (M+H)+

Workup

  1. concentrationwas concentrated
  2. customThe residue was triturated with ether
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-178e5cdd1d7746d89ffd5df5eb4e4259
Source dataset
uspto-grants-2004_11
Patent number
US06825354B2

Reaction notes

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