Tetrahydrofuran → HCID 88540940, compound
Reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18].O1CCCC1.S([O-])([O-])(=O)=S.[Na+:30].[Na+]>ClCCl.C(=O)(O)[O-].[Na+]>[Na+:30].[O:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O-:19])=[O:18]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a cooled solution (0° C.) of 16-hydroxyhexadecanoic acid (800 mg, 2.9 mmol) in dichloromethane (10 ml) and tetrahydrofurane (20 ml) Dess-Martin periodinane (1636 mg, 3.7 mmol) was added at 0° C. The mixture was stirred for 3.5 hrs at 0° C. and 2.5 hrs at room temperature under Ar-atmosphere. Then a 15%-solution of sodium thiosulfate in saturated sodium bicarbonate solution was added, the mixture was stirred at room temperature for 1.5 hrs. Intermediate 1 was extracted with diethylether, after drying over sodium sulfate the organic layer was evaporated to dryness and purified by column chromatography using silica gel as separating agent and a solvent mixture of toluene/ethylacetate. Yield: 34% (white solid).
Workup
- stirringthe mixture was stirred at room temperature for 1.5 hrs
- extractionIntermediate 1 was extracted with diethylether
- dry with materialafter drying over sodium sulfate the organic layer
- customwas evaporated to dryness
- custompurified by column chromatography
- customas separating agent
- additiona solvent mixture of toluene/ethylacetate
Sources & evidence
- ORD record
- ord-586f5234692942329152c0f9b1a2a223
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08945897B2
Reaction notes
Loading…