Triphenylphosphine → (1-{[(1-methyl-1H-imidazol-2-yl)sulfanyl]methyl}cyclobutyl)methanol

HRID 1180771Notes

Reaction equation

HRID 1180771 reaction equation
O[CH2:2][C:3]1([CH2:7][OH:8])[CH2:6][CH2:5][CH2:4]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:28][N:29]1[CH:33]=[CH:32][N:31]=[C:30]1[SH:34]>ClCCl>[CH3:28][N:29]1[CH:33]=[CH:32][N:31]=[C:30]1[S:34][CH2:2][C:3]1([CH2:7][OH:8])[CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 4498243Cyclobutane-1,1-diyldimethanolHCID 178480602HCID 178480602, compound

Product 1

HCID 11435800(1-{[(1-methyl-1H-imidazol-2-yl)sulfanyl]methyl}cyclobutyl)methanolYield 71.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.0 g (8.6 mmol) of [1-(hydroxymethyl)cyclobutyl]methanol in 20 mL of dichloromethane was added 2.48 g (9.48 mmol) of triphenylphosphine and 2.18 g (9.48 mmol) of di-tertbutylazodicarboxylate. After 5 min of stirring, 1.03 g (9.05 mmol) of 1-methyl-2-mercaptoimidazole was added as a solid. After stirring for 2 h, the reaction was concentrated under vacuum and the residue was purified using silica gel chromatography eluting with ethyl acetate:hexane (3:7) to afford 1.3 g (71%) of (1-{[(1-methyl-1H-imidazol-2-yl)sulfanyl]methyl}cyclobutyl)methanol as a yellow oil. 1H NMR (300 MHz, CDCl3) δ 6.95 (s, 1H), 6.87 (s, 1H), 6.54 (br s, 1H), 3.62 (s, 2H), 3.56 (s, 3H), 3.43 (s, 2H), 1.98-1.75 (m, 6H).

Workup

  1. stirringAfter stirring for 2 h
  2. concentrationthe reaction was concentrated under vacuum
  3. customthe residue was purified
  4. washeluting with ethyl acetate:hexane (3:7)

Sources & evidence

ORD record
ord-05505bb22d754b2983f730c46da10268
Source dataset
uspto-grants-2007_10
Patent number
US07282512B2

Reaction notes

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