Hydride → HCID 53682054, compound

HRID 429926Notes

Reaction equation

HRID 429926 reaction equation
[Si:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13](OC)=[O:14])=[CH:11][C:10]=1[CH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1>[Si:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([CH2:13][OH:14])=[CH:11][C:10]=1[CH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 166653HydrideHCID 9855836Potassium sodium tartarateHCID 18352488HCID 18352488, compound

Product 1

HCID 53682054HCID 53682054, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 100 mL 3-necked flask equipped with a magnetic stirrer and a nitrogen inlet were added 2.58 g of methyl 4-((tert-butyldimethylsilyl)oxy)-3-cyclopentylbenzoate and 15 mL of anhydrous toluene. The solution was cooled in an ice water bath and was treated with 19.3 mL of 1M diisobutylaluninum hydride in toluene (Aldrich). The solution was stirred at 0° C. for 30 min and was allowed to warm to RT. After 2 h at RT the solution was poured into 130 mL of saturated aqueous potassium sodium tartrate and the resulting mixture was stirred for 20 min. The mixture was then extracted with ethyl ether (3×70 mL). The combined ether extracts were washed with water (3×70 mL), dried over anhydrous MgSO4, and concentrated to give a cloudy oil. The crude product was purified by flash chromatography on silica gel (8:2 hexane:EtOAc) to afford 1.94 g (82%) of 4-((tert-butyldimethylsilyl)oxy)-3-cyclopentylbenzyl alcohol as a clear liquid.

Workup

  1. customTo a 100 mL 3-necked flask equipped with a magnetic stirrer and a nitrogen inlet
  2. temperatureThe solution was cooled in an ice water bath
  3. temperatureto warm to RT
  4. stirringthe resulting mixture was stirred for 20 min
  5. extractionThe mixture was then extracted with ethyl ether (3×70 mL)
  6. washThe combined ether extracts were washed with water (3×70 mL)
  7. dry with materialdried over anhydrous MgSO4
  8. concentrationconcentrated
  9. customto give a cloudy oil
  10. customThe crude product was purified by flash chromatography on silica gel (8:2 hexane:EtOAc)

Sources & evidence

ORD record
ord-dfb291f1a0584d6cb8eb8a8184583bb3
Source dataset
uspto-grants-2001_11
Patent number
US06319702B1

Reaction notes

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