Bromide ion → HCID 58424622, compound

HRID 1408817Notes

Reaction equation

HRID 1408817 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:18](=[CH:19][CH:20]=1)[O:17][C:7]1([CH2:12][CH2:11][CH:10]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:9][CH2:8]1)[CH2:6][C:5]2=[O:21].[Br-].[CH2:23]1COC[CH2:24]1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:18](=[CH:19][CH:20]=1)[O:17][C:7]1([CH2:12][CH2:11][CH:10]([C:13]([CH3:16])([CH3:14])[CH3:15])[CH2:9][CH2:8]1)[CH2:6][C:5]2([CH:23]=[CH2:24])[OH:21]

Participants

4

Reactant 3

HCID 259Bromide ionHCID 8028Tetrahydrofuran2×HCID 58423937HCID 58423937, compound

Product 1

HCID 58424622HCID 58424622, compoundYield 82%

Procedure

To a solution of 6-bromo-4′-t-butylspiro[chroman-2,1′-cyclohexan]-4-one (2.155 g, 6.13 mmol) in anhydrous THF (20 mL) at −78° C. is added a solution of vinylmagnesiun bromide in THF (1 M, 9.2 mL, 9.2 mmol) dropwise within 30 min. The reaction temperature is allowed to warm to rt and stirred for another 2 h. The reaction is chilled to 0° C. and quenched with sat. aq. NH4Cl, and extracted with ethyl acetate (2×40 mL). The combined organic phases are washed with H2O and brine, then dried over Na2SO4, and filtered. The filtrate is concentrated and the residue is purified through flash chromatography on silica gel to afford 6-bromo-4′-tert-butyl-4-vinylspiro[chroman-2,1′-cyclohexan]-4-ol as an oil (1.907 g, 82%). MS ESI+ve m/z 361 (M+H—H2O)+.

Workup

  1. temperatureThe reaction is chilled to 0° C.
  2. customquenched with sat. aq. NH4Cl
  3. extractionextracted with ethyl acetate (2×40 mL)
  4. washThe combined organic phases are washed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate is concentrated
  8. customthe residue is purified through flash chromatography on silica gel

Sources & evidence

ORD record
ord-5c4d076910bf479a8ca1994de0775444
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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