Benzoyl chloride → D-Ribitol, 1,4-dideoxy-1,4-epithio-2,3-O-(1-methylethylidene)-, 5-benzoate

HRID 1268719Notes

Reaction equation

HRID 1268719 reaction equation
[CH3:1][C:2]1([CH3:12])[O:6][C@H:5]2[CH2:7][S:8][C@H:9]([CH:10]=[O:11])[C@H:4]2[O:3]1.[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>N1C=CC=CC=1>[CH3:1][C:2]1([CH3:12])[O:6][C@H:5]2[CH2:7][S:8][C@H:9]([CH2:10][O:11][C:13](=[O:20])[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C@H:4]2[O:3]1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 86601630HCID 86601630, compound

Product 1

HCID 10859362D-Ribitol, 1,4-dideoxy-1,4-epithio-2,3-O-(1-methylethylidene)-, 5-benzoateYield 99%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 111 (2.1 g, 11.1 mmol) in pyridine (20 mL) was added benzoyl chloride (1.9 g, 13.4 mmol) at 0° C. and the reaction mixture was stirred for 6 h at room temperature before being quenched with methanol. The reaction mixture was evaporated under reduced pressure. The residue was then taken up in diethyl ether (50 mL), and the pyridinium salt was filtered and washed with diethyl ether. The combined organic layer was concentrated and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=4:1) to afford the benzoate 112 (3.2 g, 99%) as a colorless oil: 1H NMR (CDCl3) δ 1.26 (s, 3H, CH3), 1.47 (s, 3H, CH3), 2.87 (dd, 1H, J=13.2, 1.5 Hz, 6-CHH), 3.11 (dd, 1H, J=13.2, 4.9 Hz, 6–CHH), 3.57 (m, 1H, 4-H), 4.25 (dd, 1H, J=11.5, 8.0 Hz, BzOCHH), 4.35 (dd, 1H, J=11.4, 5.8 Hz, BzOCHH), 4.72 (dd, 1H, J=5.6, 1.2 Hz, 6a-H), 4.91 (td, 1H, J=4.4, 1.2 Hz, 3a-H), 7.35–7.99 (m, 5H, Ph); FAB-MS m/z 294 (M+); Anal. Calcd for C15H18O4S: C, 61.20; H, 6.16; S, 10.89. Found: C, 60.99; H, 6.42; S, 10.77.

Workup

  1. custombefore being quenched with methanol
  2. customThe reaction mixture was evaporated under reduced pressure
  3. filtrationthe pyridinium salt was filtered
  4. washwashed with diethyl ether
  5. concentrationThe combined organic layer was concentrated
  6. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=4:1)

Sources & evidence

ORD record
ord-67efb869a3ac478a986ff4df461b4370
Source dataset
uspto-grants-2007_04
Patent number
US07199127B2

Reaction notes

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