Sodium hydride → HCID 14653182, compound

HRID 1608084Notes

Reaction equation

HRID 1608084 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C@@H:5]([C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1)[OH:6].[H-].[Na+]>C1COCC1.[Ni]>[Br:13][C:10]1[CH:11]=[CH:12][C:7]([C@@H:5]2[CH2:4][CH2:3][CH2:2][O:6]2)=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 14653151HCID 14653151, compound

Product 1

HCID 14653182HCID 14653182, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of [S]-1-chloro-4-(4-bromophenyl)-4-butanol (50 mmol) in THF (25 ml) was added to a cooled suspension (0° C.) of NaH (55 mmol) in THF (50 ml). After being stored for 2 h at 25C., the reaction mixture was quenched with water, brought to pH 6 with concentrated HC1, and extracted with ether (2×50 ml). The organic phase was dried over H2SO4, filtered and all volatiles removed under reduced pressure. The residue was distilled to provide the product in 75% yield, 98%ee as determined on a chiral capillary column of Ni(HFN--IR--Cam)2.

Workup

  1. custom, the reaction mixture was quenched with water
  2. extractionextracted with ether (2×50 ml)
  3. dry with materialThe organic phase was dried over H2SO4
  4. filtrationfiltered
  5. customall volatiles removed under reduced pressure
  6. distillationThe residue was distilled
  7. customto provide the product in 75% yield, 98%ee

Sources & evidence

ORD record
ord-ab7d4b3cdddf4479976395d9f7e25688
Source dataset
uspto-grants-1989_09
Patent number
US04868344

Reaction notes

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