Sodium hydride → HCID 18474995, compound

HRID 2227889Notes

Reaction equation

HRID 2227889 reaction equation
[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([OH:21])[C:17]([O:19][CH3:20])=[O:18])=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:25][C:26]1[CH:38]=[CH:37][C:29]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[CH:28][CH:27]=1>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Si:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH:16]([O:21][CH2:25][C:26]2[CH:27]=[CH:28][C:29]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[CH:37][CH:38]=2)[C:17]([O:19][CH3:20])=[O:18])=[CH:13][CH:14]=1)([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 11414578Tert-butyl 4-(bromomethyl)benzoateHCID 18475011HCID 18475011, compound

Product 1

HCID 18474995HCID 18474995, compoundYield 41.2%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-40 °C

Procedure

A solution of methyl 3-(4-tert-butyldimethylsilyloxyphenyl)-2-hydroxypropionate (300 mg, 0.97 mmol) in THF (2 ml) at −78° C. was treated with a suspension of sodium hydride (60%, 40 mg, 1 mmol) in THF (1 ml). The mixture was stirred at −40° C. for 15 minutes, then tetrabutyl ammonium iodide (20 mg) and tert-butyl 4-bromomethylbenzoate (270 mg, 0.97mmol) dissolved in THF (1 ml) were added. After the cooling bath was removed, the mixture was stirred for 16 hours, quenched with saturated aqueous ammonium chloride and diluted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel (hexane:ethyl acetate=85:15) to give the title material (200 mg, 41%) as a colorless oil.

Workup

  1. additionwere added
  2. customAfter the cooling bath was removed
  3. stirringthe mixture was stirred for 16 hours
  4. customquenched with saturated aqueous ammonium chloride
  5. additiondiluted with ethyl acetate
  6. washThe organic phase was washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was chromatographed on silica gel (hexane:ethyl acetate=85:15)

Sources & evidence

ORD record
ord-f4762ad50a244149916da116ce0588ae
Source dataset
uspto-grants-2002_07
Patent number
US06414179B1

Reaction notes

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