Ethyl bromoacetate → HCID 58640415, compound

HRID 1350854Notes

Reaction equation

HRID 1350854 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:14])[C:12]2[C:7](=[CH:8][C:9]([OH:13])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1.Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>O1CCCC1>[CH3:3][C:4]1([CH3:14])[C:12]2[C:7](=[CH:8][C:9]([O:13][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 23014065HCID 23014065, compound

Product 1

HCID 58640415HCID 58640415, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of 60% sodium hydride (240 mg, 5.87 mmol) in anhydrous tetrahydrofuran (5 ml) was added a solution of crude 1,1-dimethylindan-5-ol (878 mg) in anhydrous tetrahydrofuran (10 ml) dropwise at 0° C. After 15 minutes at 0° C., to this was added ethyl bromoacetate (1.16 g, 6.94 mmol) via a syringe at 0° C. After 2 hours at ambient temperature, the mixtute was quenched with water (15 ml) and extracted with ethyl acetate. The combined solution was washed with brine, dried over sodium sulfate. After filtration to separate solvent and sodium sulfate, the solvent was removed under reduced pressure to give a residue, which was applied to a silica gel chromatography column and eluted with hexane/ethyl acetate=8/1–6/1 to furnish 890 mg (67% yield in 2 steps) of the title compound as a pale yellow oil.

Workup

  1. waitAfter 2 hours at ambient temperature
  2. customthe mixtute was quenched with water (15 ml)
  3. extractionextracted with ethyl acetate
  4. washThe combined solution was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration
  7. customto separate solvent and sodium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customto give a residue, which
  10. washeluted with hexane/ethyl acetate=8/1–6/1

Sources & evidence

ORD record
ord-4b50cc47f1a843eba9b7498f9e7bdf90
Source dataset
uspto-grants-2007_05
Patent number
US07214824B2

Reaction notes

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