Pentane → HCID 22568974, compound

HRID 395150Notes

Reaction equation

HRID 395150 reaction equation
Br[C:2]1[CH:18]=[CH:17][C:5]([O:6][Si:7]([CH:14]([CH3:16])[CH3:15])([CH:11]([CH3:13])[CH3:12])[CH:8]([CH3:10])[CH3:9])=[CH:4][C:3]=1[C:19]([CH3:22])([CH3:21])[CH3:20].C([Li])(C)(C)C.CCCCC.Cl[C:34]([O:36][CH2:37][CH3:38])=[O:35]>CCOCC>[C:19]([C:3]1[CH:4]=[C:5]([O:6][Si:7]([CH:14]([CH3:16])[CH3:15])([CH:11]([CH3:12])[CH3:13])[CH:8]([CH3:9])[CH3:10])[CH:17]=[CH:18][C:2]=1[C:34]([O:36][CH2:37][CH3:38])=[O:35])([CH3:22])([CH3:20])[CH3:21]

Participants

6

Reactant 4

HCID 8003PentaneHCID 10928Ethyl chloroformateHCID 22568937HCID 22568937, compound2×HCID 178418306HCID 178418306, compound

Product 1

HCID 22568974HCID 22568974, compoundYield 124.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of (4-bromo-3-tert-butyl-phenoxy)-triisopropyl-silane (Intermediate 105, 1.00 g, 2.60 mmols) in 15 mL Et2O cooled to −78° C. was added 3.6 mL of tert-butyllithium, 1.7 M in pentane (395.0 mg, 6.2 mmols). After stirring for 30 minutes ethyl chloroformate (607.6 mg, 5.6 mmols) was added. The resulting solution was warmed to room temperature and quenched by the addition of saturated aqueous NH4Cl. The mixture was extracted with EtOAc and the combined organic layers dried (MgSO4) concentrated under reduced pressure The residue was chromatographed (2-5% EtOAc-hexanes) to give 1.23 g (88%) of the title compound as a colorless oil.

Workup

  1. additionwas added
  2. customquenched by the addition of saturated aqueous NH4Cl
  3. extractionThe mixture was extracted with EtOAc
  4. dry with materialthe combined organic layers dried (MgSO4)
  5. concentrationconcentrated under reduced pressure The residue
  6. customwas chromatographed (2-5% EtOAc-hexanes)

Sources & evidence

ORD record
ord-8ac3b3da8376425baf74d8e350b7c363
Source dataset
uspto-grants-2003_08
Patent number
US06603019B2

Reaction notes

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