Tetrahydrofuran → (1S,4aS,7aR)-1-[1-(ethoxy)ethoxy]-7-[2-(hydroxy)ethyl]-1,4a,5,7a-tetrahydrocyclopenta[c]pyrane-4-carboxylic acid methylester
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[C@H:6]2[CH2:19][CH:18]=[C:17]([CH:20]=O)[C@@H:7]2[C@H:8]([O:11][CH:12]([O:14][CH2:15][CH3:16])[CH3:13])[O:9][CH:10]=1)=[O:4].CI.[Mg].[Cl-].[NH4+].[O:27]1CCC[CH2:28]1>>[CH3:1][O:2][C:3]([C:5]1[C@H:6]2[CH2:19][CH:18]=[C:17]([CH2:20][CH2:28][OH:27])[C@@H:7]2[C@H:8]([O:11][CH:12]([O:14][CH2:15][CH3:16])[CH3:13])[O:9][CH:10]=1)=[O:4]Participants
Conditions
- Temperature
- -78 °C
Procedure
An anhydrous tetrahydrofuran solution containing 100 mg of (1S,4aS,7aR)-1-[1-(ethoxy) ethoxy]-7-formyl-1,4a,5,7a-tetrahydrocyclopenta [c] pyrane-4-carboxylic acid methylester was cooled to −78 ° C. under argon gas atmosphere followed by dropping 0.38 ml of magnesium methyliodide (0.98 M tetrahydrofuran solution). Two hours later, saturated aqueous ammonium chloride solution was added to the reaction mixture followed by extraction with ethyl acetate. After washing the organic phase with brine, it was dried over magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel chromatography to obtain a pale yellow oil from the hexane-ether eluate in the form of (1S,4aS,7aR)-1-[1-(ethoxy) ethoxy]-7-[2-(hydroxy) ethyl]-1,4a,5,7a-tetrahydrocyclopenta [c] pyrane-4-carboxylic acid methylester (81 mg, yield: 77%). The physicochemical properties of this compound are described below.
Workup
- extractionfollowed by extraction with ethyl acetate
- washAfter washing the organic phase with brine, it
- dry with materialwas dried over magnesium sulfate
- distillationAfter distilling off the solvent under reduced pressure
- customthe residue was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-f6bb75f0ab494c1695530496d0b3a330
- Source dataset
- uspto-grants-2001_05
- Patent number
- US06225478B1
Reaction notes
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