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

HRID 571063노트

반응식

HRID 571063 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

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, 110 mmol) at r.t. and the mixture was stirred for 1 h. The reaction mixture was poured onto ice-water and more Et2O was added. Then the Et2O phase was collected and water phase was extracted by Et2O twice, the combined Et2O layer was washed with brine, dried over Na2SO4, 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), 6.55 (s, 1H), 4.92 (s, 2H), 4.65 (s, 2H). MS (M+H)+ 250.1/252.1.

후처리

  1. additionwas added
  2. customThen the Et2O phase was collected
  3. extractionwater phase was extracted by Et2O twice
  4. washthe combined Et2O layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-7615938a76884ad1b976d4abd7a643f5
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09024032B2

반응 노트

불러오는 중…