Sulfuric Acid → [(1R,2R)-3,3-diethoxy-2-(hydroxymethyl)cyclobutyl]methanol
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:9][C:10]1([O:24][CH2:25][CH3:26])[CH2:13][C@@H:12]([C:14](OCC)=[O:15])[C@@H:11]1[C:19](OCC)=[O:20])[CH3:8].[Cl-].[NH4+].S(=O)(=O)(O)O>C1COCC1.CCOCC>[CH2:25]([O:24][C:10]1([O:9][CH2:7][CH3:8])[CH2:13][C@@H:12]([CH2:14][OH:15])[C@@H:11]1[CH2:19][OH:20])[CH3:26]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a suspension of lithium aluminum hydride (2.38 g, 0.0627 mol) in dry THF (50 ml) was added slowly (trans)-3,3-diethoxy-1,2-cyclobutanedicarboxylic acid, diethyl ester (11.29 g, 0.0392 mol) in THF (25 ml) so that a gentle reflux was maintained. The reaction was heated at 55° for 4 hours and then diluted with ether (100 ml) and poured into saturated aqueous ammonium chloride (100 ml). The pH was lowered to 4 with 3M sulfuric acid. The suspension was extracted with ether (4×100 ml) and then chloroform (3×100 ml). The ether extracts were combined, dried over sodium sulfate, filtered and concentrated to give 5.613 g of desired product. The chloroform extracts were combined, dried over sodium sulfate, filtered and concentrated to give 112 mg of additional desired product.
Workup
- temperaturea gentle reflux
- temperaturewas maintained
- temperatureThe reaction was heated at 55° for 4 hours
- extractionThe suspension was extracted with ether (4×100 ml)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-13164b9c1ae04b6296d0ff8ccbcee68d
- Source dataset
- uspto-grants-1992_06
- Patent number
- US05126345
Reaction notes
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