Ethyl Acetate → HCID 86751603, compound

HRID 2293696Notes

Reaction equation

HRID 2293696 reaction equation
[CH:1]1([CH:4]([C:6]2[O:7][C:8]([CH2:11][OH:12])=[CH:9][CH:10]=2)O)[CH2:3][CH2:2]1.[O:13]1[C:18](=[O:19])[CH:17]=[CH:16][C:15]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=[CH:25][C:14]1=2.CC[O:28]C(C)=O>C(Cl)Cl.FC(F)(F)C(O)=O>[CH:1]1([CH2:4][C:6]2([C:17]3[C:18](=[O:19])[O:13][C:14]4[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][C:15]=4[C:16]=3[OH:28])[O:7][C:8]([CH2:11][OH:12])=[CH:9][CH2:10]2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 54192227HCID 54192227, compoundHCID 178515731HCID 178515731, compound

Product 1

HCID 86751603HCID 86751603, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

Cyclopropyl (5-hydroxymethylfuran-2-yl) carbinol of Preparation 66 (336 mg) and 2H-cycloocta[b]pyran-2-one of formula JJ-3 (427 mg) are dispersed in methylene chloride (25 mL) at 23° C. and trifluoroacetic acid (4 drops) is added. The reaction is stirred for 2.5 h, then poured into EtOAc (400 mL) and washed with water (2×50 mL) and brine. Drying over MgSO4, filtration and concentration in vacuo affords a yellow foam. The product is isolated via column chromatography (150 g silica gel), eluting with 30% EtOAc in CH2Cl2, giving the title product (275 mg) as a white foam.

Workup

  1. washwashed with water (2×50 mL) and brine
  2. dry with materialDrying over MgSO4, filtration and concentration in vacuo
  3. customaffords a yellow foam
  4. customThe product is isolated via column chromatography (150 g silica gel)
  5. washeluting with 30% EtOAc in CH2Cl2

Sources & evidence

ORD record
ord-cb15d68727754b35b71b56a8c1567ea6
Source dataset
uspto-grants-1997_11
Patent number
US05686486

Reaction notes

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