Benzyl Alcohol → HCID 17825616, compound

HRID 1297035Notes

Reaction equation

HRID 1297035 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].Cl>CN(C=O)C>[CH2:3]([O:10][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 264813Ethyl 8-bromooctanoate

Product 1

HCID 17825616HCID 17825616, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

403 mg (10.1 mmol) of sodium hydride (60% oily) was added to 1.102 g (10.2 mmol) of benzyl alcohol in 15 ml of DMF, and they were stirred for 30 minutes. 2.51 g (9.99 mmol) of ethyl 8-bromooctanoate was dissolved in 5 ml of DMF, and the obtained solution was added dropwise to the reaction mixture in ice bath. After stirring at room temperature for 1.5 hours, 2 N hydrochloric acid was added to the mixture. DMF was evaporated under reduced pressure. After the extraction with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=9/1/) to obtain the title compound.

Workup

  1. additionthe obtained solution was added dropwise to the reaction mixture in ice bath
  2. stirringAfter stirring at room temperature for 1.5 hours
  3. customDMF was evaporated under reduced pressure
  4. extractionAfter the extraction with ethyl acetate
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=9/1/)

Sources & evidence

ORD record
ord-28e4b957604f477c9d145d5aadb941f9
Source dataset
uspto-grants-2007_07
Patent number
US07247645B2

Reaction notes

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