Dichloromethane → 3-Acetoxyestra-1,3,5(10)-trien-17-one-2-carboxaldehyde
Reaction equation
[OH:1][C:2]1[C:19]([CH:20]=[O:21])=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C:11](=[O:22])[CH2:10][CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1.C(Cl)Cl.C(N(CC)CC)C.[C:33](OC(=O)C)(=[O:35])[CH3:34]>O>[C:33]([O:1][C:2]1[C:19]([CH:20]=[O:21])=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C:11](=[O:22])[CH2:10][CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1)(=[O:35])[CH3:34]Participants
6
Procedure
To a solution of 3-hydroxyestra-1,3,5(10)-trien-17-one-2-carboxaldehyde (60, 1.92 g, 6.43 mmol) of CH2Cl2 (30 mL) was added triethylamine (2.3 mL, 16 mmol) and acetic anhydride (0.94 mL, 9.6 mmol) at room temperature. The reaction mixture was stirred for 16 h, H2O was added, and the mixture was extracted with EtOAc. The combined organic layers were washed with H2O, saturated aqueous NaCl, and then dried (Na2SO4). The desiccant was filtered and the solvent was evaporated at reduced pressure. The residue was purified by column chromatography (silica gel) using n-hexane:EtOAc (2:1→3:2, v/v) to afford 2.08 g of 61 (95% yield) mp: 179-181° C.
Workup
- extractionthe mixture was extracted with EtOAc
- washThe combined organic layers were washed with H2O, saturated aqueous NaCl
- dry with materialdried (Na2SO4)
- filtrationThe desiccant was filtered
- customthe solvent was evaporated at reduced pressure
- customThe residue was purified by column chromatography (silica gel)
Sources & evidence
- ORD record
- ord-0e5bee6a13904ee988863f0f20810a92
- Source dataset
- uspto-grants-2000_04
- Patent number
- US06046186
Reaction notes
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