3-Thiocresol → HCID 21963745, compound

HRID 2212075Notes

Reaction equation

HRID 2212075 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.[CH3:9][CH:10]([CH:13]=[CH2:14])[CH2:11]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>ClCCl>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8][CH2:9][CH:10]([CH3:11])[CH:13]=[CH2:14])[CH:3]=1

Participants

6

Reactant 4

HCID 79303-ThiocresolHCID 11776TriphenylphosphineHCID 942922-Methyl-3-buten-1-olHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 21963745HCID 21963745, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-methylbenzenethiol (1.80 ml, 23.82 mmol), 2-methyl-3-buten-1-ol (2.73 ml, 26.47 mmol) and triphenylphosphine (6.94 g, 26.47 mmol) in dichloromethane (10 ml) was treated with diethyl azodicarboxylate (4.59 ml, 29.12 mmol) at room temperature. The mixture was concentrated in vacuo and dissolved in diethyl ether to remove triphenylphosphine oxide. The organic phase was purified by flash column chromatography on silica, eluting with hexane, to afford the title compound as a clear oil (1.01 g, 20%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutiondissolved in diethyl ether
  3. customto remove triphenylphosphine oxide
  4. customThe organic phase was purified by flash column chromatography on silica
  5. washeluting with hexane

Sources & evidence

ORD record
ord-7b7e319387474039ae1a7e316b7f9a5e
Source dataset
uspto-grants-2006_09
Patent number
US07101892B2

Reaction notes

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