Bromide ion → HCID 58424797, compound

HRID 2096629Notes

Reaction equation

HRID 2096629 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[O:13][C:7]1([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)[CH2:6][C:5]2=[O:17].[Br-].[CH2:19]1COC[CH2:20]1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[O:13][C:7]1([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1)[CH2:6][C:5]2([CH:19]=[CH2:20])[OH:17]

Participants

4

Reactant 3

HCID 259Bromide ionHCID 8028Tetrahydrofuran2×HCID 10541879HCID 10541879, compound

Product 1

HCID 58424797HCID 58424797, compound

Procedure

To a solution of 6-bromospiro[chroman-2,1′-cyclohexan]-4-one (383 mg, 1.30 mmol) in anhydrous THF (10 mL) at −78° C. is added a solution of vinylmagnesiun bromide in THF (1 M, 1.95 mL, 1.95 mmol) dropwise within 10 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 (2×30 mL). The combined organic phases are washed with H2O, brine, dried over Na2SO4, and filtered. The filtrate is concentrated to give crude 6-bromo-4-vinylspiro[chroman-2,1′-cyclohexan]-4-ol as an oil, which is used for the next step without further purification. MS ESI +ve m/z 305 (M+H—H2O)+.

Workup

  1. temperatureThe reaction is chilled to 0° C.
  2. customquenched with sat. aq. NH4Cl
  3. extractionextracted with ethyl acetate (2×30 mL)
  4. washThe combined organic phases are washed with H2O, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-b0305b1e4ca24993a856fbe5a61b5dd7
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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