Thionyl Chloride → 5-(benzyloxy)-2-(chloromethyl)-4H-pyran-4-one

HRID 1056895Notes

Reaction equation

HRID 1056895 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:17])[CH:11]=[C:12]([CH2:15]O)[O:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=S(Cl)[Cl:20]>CCOCC>[CH2:1]([O:8][C:9]1[C:10](=[O:17])[CH:11]=[C:12]([CH2:15][Cl:20])[O:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 9015985-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one

Product 1

HCID 37033215-(benzyloxy)-2-(chloromethyl)-4H-pyran-4-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a suspension of 5-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one (18.5 g, 80 mmol) in Et2O (130 mL) was added SOCl2 (18 mL, 1 10 mmol) at r.t. and the mixture was stirred for 1 h. The reaction mixture was poured onto ice-water and more Et20 was added. Then the Et20 phase was collected and water phase was extracted by Et20 twice, the combined Et20 layer was washed with brine, dried over Na2S04, and concentrated. The residue was purified by silica gel chromatography to give 5-(benzyloxy)-2-(chloromethyl)-4H-pyran-4-one 1HNMR (DMSO, 400 MHZ) δ 8.27 (s, 1H), 7.32-7.41 (m, 5H)S 6.55 (s, 1H), 4.92 (s, 2H), 4.65 (s, 2H). MS (M+H)+250.1/252.1.

Workup

  1. additionThe reaction mixture was poured onto ice-water and more Et20
  2. additionwas added
  3. customThen the Et20 phase was collected
  4. extractionwater phase was extracted by Et20 twice
  5. washthe combined Et20 layer was washed with brine
  6. customdried over Na2S04
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-21b3fb542d7e4168bb1f8138517cca5b
Source dataset
uspto-grants-2016_07
Patent number
US09399651B2

Reaction notes

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