Benzyl Alcohol → (3aR,6aS)-2-(Benzyloxy)-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-5-carbaldehyde

HRID 593396

반응식

HRID 593396 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.[CH2:12](O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[O-]S([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[CH2:12]([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)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

5

반응물 3

HCID 244Benzyl AlcoholHCID 24083Sulfuric acid magnesium salt (1:1)HCID 72703147(3aR,6aS)-2-Hydroxy-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-5-carbaldehyde

생성물 1

HCID 118117763(3aR,6aS)-2-(Benzyloxy)-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-5-carbaldehyde

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. Benzyl alcohol (794.1 μL, 7.68 mmol, 2 eq.) was added via syringe and amberlyst 15 (56.5 mg) and MgSO4 (1.16 g) were added as solids. The reaction mixture was stirred at r.t. for 36 h. The reaction mixture was filtered through a sinter funnel and the solids washed with CH2Cl2 (2×10 ml). The filtrate was concentrated under reduced pressure to give the crude material which was purified by column chromatography eluting with petrol/EtOAc (9:1) to give the benzyl acetal 56 (as an approximately 1.5:1 mixture of diasteroisomers, 657.8 mg, 70%) as pale yellow oil.

후처리

  1. stirringThe reaction mixture was stirred at r.t. for 36 h
  2. filtrationThe reaction mixture was filtered through a sinter funnel
  3. washthe solids washed with CH2Cl2 (2×10 ml)
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto give the crude material which
  6. customwas purified by column chromatography
  7. washeluting with petrol/EtOAc (9:1)

출처 및 근거

ORD 기록
ord-42e72c3589d84cb0b8d84392dc20ca15
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242954B2

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