Hydrochloric Acid → HCID 68861307, compound

HRID 1726029Notes

Reaction equation

HRID 1726029 reaction equation
[H-].[Na+].[OH:3][CH:4]1[CH2:9][CH2:8][O:7][C:5]1=[O:6].Br[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl>CN(C=O)C>[C:13]1([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:11][O:3][CH:4]1[CH2:9][CH2:8][O:7][C:5]1=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 2633651-(Bromomethyl)-2-phenylbenzeneHCID 545831alpha-Hydroxy-gamma-butyrolactone

Product 1

HCID 68861307HCID 68861307, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.43 g, 10.8 mmol) is added portionwise to a solution of α-hydroxy-γ-butyrolactone (1 g, 9.8 mmol) in DMF (15 ml) at 0° C. under a nitrogen atmosphere. 2-Bromomethylbiphenyl (2.42 g, 9.8 mmol) is then rapidly added. The reaction medium is stirred for 2 hours at room temperature and is then treated by adding 1N hydrochloric acid solution (10 ml). The aqueous phase is extracted with ethyl acetate (2×20 ml) and the combined organic phases are washed with water (4×15 ml), dried over sodium sulphate, filtered and concentrated. After purification by flash chromatography (2/1 heptane/EtOAc), the expected compound is obtained in the form of a colourless oil (1.32 g, 50%).

Workup

  1. additionis then treated
  2. extractionThe aqueous phase is extracted with ethyl acetate (2×20 ml)
  3. washthe combined organic phases are washed with water (4×15 ml)
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customAfter purification by flash chromatography (2/1 heptane/EtOAc)

Sources & evidence

ORD record
ord-8bb6361cc4b64d0aa1968b1d897c9434
Source dataset
uspto-grants-2009_02
Patent number
US07491747B2

Reaction notes

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