4-Toluenesulfonyl chloride → HCID 86642194, compound

HRID 2385019Notes

Reaction equation

HRID 2385019 reaction equation
[CH2:1]([O:8][CH2:9][O:10][C@@H:11]([CH3:14])[CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>ClCCl.N1C=CC=CC=1.C(OCC)(=O)C>[CH3:25][C:15]1[CH:20]=[CH:19][C:18]([S:21]([O:13][CH2:12][C@@H:11]([O:10][CH2:9][O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH3:14])(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

6

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 6711346HCID 6711346, compound

Product 1

HCID 86642194HCID 86642194, compoundYield 85.6%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (2S)-2-[(benzyloxy)methoxy]propan-1-ol (Banfi, L., et al., J. Org. Chem. (1984), 49:3784-90) (11.40 g, 0.058 mol) in dichloromethane (50 mL) and pyridine (20 mL) was added p-toluenesulfonyl chloride (11.0 g, 0.057 mol) at 0° C. The reaction mixture was stirred at ambient temperature for 20 h, diluted with ethyl acetate and washed with water, 5% hydrochloric acid solution, water and brine; dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo. The residue was purified by column chromatography to afford (S)-2-(benzyloxymethoxy)propyl 4-methylbenzenesulfonate (17.10 g, 84%): 1H NMR (300 MHz, CDCl3) 7.77 (d, J=8.3 Hz, 2H), 7.36-7.25 (m, 7H), 4.71 (s, 2H), 4.59-4.48 (m, 2H), 4.02-3.93 (m, 3H), 2.41 (s, 3H), 1.19-1.11 (m, 3H).

Workup

  1. washwashed with water, 5% hydrochloric acid solution, water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-8a670e20ae4449ecbf0553c82d5caf59
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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