Hexane → HCID 18352482, compound

HRID 429928Notes

Reaction equation

HRID 429928 reaction equation
C(OP([CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[Si:19]([O:26][C:27]1[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][C:28]=1[CH:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].CCCCCC>CCOCC.CCOC(C)=O>[Si:19]([O:26][C:27]1[CH:34]=[CH:33][C:30](/[CH:31]=[CH:9]/[C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])=[CH:29][C:28]=1[CH:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1)([C:22]([CH3:24])([CH3:25])[CH3:23])([CH3:21])[CH3:20]

Participants

7

Reactant 4

HCID 8058HexaneHCID 24758Sodium hydrideHCID 2773685tert-Butyl diethylphosphonoacetateHCID 18352505HCID 18352505, compound

Product 1

HCID 18352482HCID 18352482, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a 100 mL 3-necked flask equipped with a magnetic stirrer, a nitrogen inlet and a reflux condenser were added 1.57 g of tert-butyl diethylphosphonoacetate (Aldrich) and 20 mL of anhydrous ethyl ether. This was followed by addition of 0.40 g of 60% NaH mineral oil dispersion. The resulting cloudy solution was heated at reflux for 25 min, cooled to 0° C. and treated with a solution of 1.52 g of 4((tert-butyldimethylsilyl)oxy)-3-cyclopentylbenzaldehyde in 10 mL of ether. A thick yellow gel resulted which was broken up with a spatula. The mixture was allowed to warm to RT and stirring was continued for an additional 1 h Analysis by tic (SiO2, 95:5 hexane:EtOAc) indicated a major new component at Rf=0.48 and minor components at Rf=0.06, 0.41 and 0.98. The mixture was diluted with 70 mL of ether, washed with saturated brine, and dried over anhydrous MgSO4. The drying agent was removed by filtration and the filtrate concentrated to give a yellow oil. This material was purified by flash chromatography on silica gel (97:3 hexaneEtOAc) to afford 1.53 g (77%) of tert-butyl trans-4-((tert-butyldimethylsilyl)oxy)-3-cyclopentylcinramate as a clear oil.

Workup

  1. customTo a 100 mL 3-necked flask equipped with a magnetic stirrer, a nitrogen inlet and a reflux condenser
  2. temperatureThe resulting cloudy solution was heated
  3. temperatureat reflux for 25 min
  4. customA thick yellow gel resulted which
  5. temperatureto warm to RT
  6. washwashed with saturated brine
  7. dry with materialdried over anhydrous MgSO4
  8. customThe drying agent was removed by filtration
  9. concentrationthe filtrate concentrated
  10. customto give a yellow oil
  11. customThis material was purified by flash chromatography on silica gel (97:3 hexaneEtOAc)
  12. customto afford 1.53 g (77%) of tert-butyl trans-4-((tert-butyldimethylsilyl)oxy)-3-cyclopentylcinramate as a clear oil

Sources & evidence

ORD record
ord-3a0a46aef6194b63ac398c9bd3232db7
Source dataset
uspto-grants-2001_11
Patent number
US06319702B1

Reaction notes

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