Hexane → HCID 18352505, compound

HRID 369818Notes

Reaction equation

HRID 369818 reaction equation
[Si:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][C:10]=1[CH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.CCCCCC.CCOC(C)=O>C(Cl)Cl>[Si:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[CH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 53682054HCID 53682054, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 18352505HCID 18352505, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.94 g of 4-((tert-butyldimethylsilyl)oxy)-3-cyclopentylbenzyl alcohol in 70 mL of anhydrous CH2Cl2 was treated with 2.05 g of pyridinium chlorochromate (Aldrich) and was stirred at RT under nitrogen. After 30 min, tlc (SiO2, 85:15 hexane:EtOAc) indicated no remaining starting material and a major new component at Rf =0.80. The mixture was filtered to remove solids and the filtrate was washed with 5% aqueous citric acid (4×50 mL) followed by 5% aqueous NaHCO3 (4×50 mL). The CH2Cl2 solution was dried over anhydrous MgSO4 and concentrated in vacuo to give a brown oil. This material was purified by flash chromatography on silica gel (9:1 hexane:EtOAc) to afford 1.52 g (79%) of 4-((tert-butyldimethylsilyl)oxy)-3-cyclopentylbenzaldehyde as a clear oil.

Workup

  1. filtrationThe mixture was filtered
  2. customto remove solids
  3. washthe filtrate was washed with 5% aqueous citric acid (4×50 mL)
  4. dry with materialThe CH2Cl2 solution was dried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give a brown oil
  7. customThis material was purified by flash chromatography on silica gel (9:1 hexane:EtOAc)

Sources & evidence

ORD record
ord-19b20f87fce44aa5aab8beae7ad39816
Source dataset
uspto-grants-2000_10
Patent number
US06140100

Reaction notes

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