Triphenylphosphine → 2-Octanol

HRID 1162874Notes

Reaction equation

HRID 1162874 reaction equation
[CH3:1][CH:2]([OH:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:29][NH:30][S:31]([C:34]1[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=1)(=[O:33])=[O:32].COCCOC(N=NC(OCCOC)=O)=O>C1COCC1>[CH3:40][C:37]1[CH:38]=[CH:39][C:34]([S:31]([N:30]([CH3:29])[CH:2]([CH3:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])(=[O:33])=[O:32])=[CH:35][CH:36]=1.[CH3:1][CH:2]([OH:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 12543Benzenesulfonamide, N,4-dimethyl-HCID 200832-OctanolHCID 533844152-methoxyethyl N-(2-methoxyethoxycarbonylimino)carbamate

Product 2

HCID 200832-OctanolHCID 11055596N,4-dimethyl-N-octan-2-ylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

After (racemic)-2-octanol (300 mg, 2.30 mmol), triphenylphosphine (727 mg, 2.76 mmol), N-methyl-p-toluenesulfonamide (514 mg, 2.76 mmol), and THF (12 ml) were added to a 50 ml flask, azodicarboxylic acid bis(2-methoxyethyl) ester (648 mg, 2.76 mmol) dissolved in THF (6 ml) was added dropwise thereto at 20° C., and the reaction was allowed to proceed for 21 hours. Subsequently, a crude product obtained by concentration was purified by column chromatography (silica gel, 10% ethyl acetate-hexane solution) to give 4,N-dimethyl-N-(1-methylheptyl)benzenesulfonamide as a white solid substance (223 mg, yield: 33%/(racemic)-2-octanol).

Workup

  1. additionwas added dropwise
  2. customat 20° C.
  3. customSubsequently, a crude product obtained by concentration
  4. customwas purified by column chromatography (silica gel, 10% ethyl acetate-hexane solution)

Sources & evidence

ORD record
ord-0aa07f108c494dc6a76cdc33f2ad7e35
Source dataset
uspto-grants-2010_10
Patent number
US07820802B2

Reaction notes

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