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

HRID 593395

反応式

HRID 593395 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ea547e51e76a4a729a318e3fdc178037
出典データセット
uspto-grants-2016_01
特許番号
US09242954B2

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