Benzoyl chloride → (3aR,6aS)-5-Formyl-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-yl benzoate

HRID 593395

반응식

HRID 593395 반응식
[OH:1][CH:2]1[O:6][C@H:5]2[CH2:7][C:8]([CH:10]=[O:11])=[CH:9][C@H:4]2[CH2:3]1.CN(C1C=CC=CN=1)C.C(N(CC)CC)C.[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)Cl>[C:28]([O:1][CH:2]1[O:6][C@H:5]2[CH2:7][C:8]([CH:10]=[O:11])=[CH:9][C@H:4]2[CH2:3]1)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

참가 물질

6

반응물 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 72703147(3aR,6aS)-2-Hydroxy-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-5-carbaldehyde

생성물 1

HCID 90019505(3aR,6aS)-5-Formyl-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-yl benzoate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Purified lactol 7 (591.5 mg, 3.84 mmol, 1 eq.), was dissolved in CH2Cl2 (7 ml) and stirred at r.t. Dimethylaminopyridine (23.5 mg, 0.19 mmol, 5 mol %) was added as a solid. Triethylamine (647.5 μl, 4.61 mmol, 1.2 eq.) and benzoyl chloride (534.5 μL, 4.61 mmol, 1.2 eq.) were added via syringe. The reaction mixture was stirred at r.t. for 36 h, filtered over basic alumina and the organic phase was concentrated to give the crude material. The material was purified by column chromatography eluting with petrol/EtOAc (3:1) to give the benzoyl acetal 55 (as an approximately 1.3:1 mixture of diasteroisomers, 706.7 mg, 71%) as pale yellow solid.

후처리

  1. stirringThe reaction mixture was stirred at r.t. for 36 h
  2. filtrationfiltered over basic alumina
  3. concentrationthe organic phase was concentrated
  4. customto give the crude material
  5. customThe material was purified by column chromatography
  6. washeluting with petrol/EtOAc (3:1)

출처 및 근거

ORD 기록
ord-ea547e51e76a4a729a318e3fdc178037
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242954B2

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