Bromide ion → HCID 57803572, compound

HRID 2103042Notes

Reaction equation

HRID 2103042 reaction equation
[CH3:1][C:2]1[C:14]([O:15]C2CCCCO2)=[C:13]([CH3:22])[C:12]([CH:23]=O)=[C:11]2[C:3]=1[CH2:4][CH2:5][C:6]1(O2)[CH2:9][CH2:8][CH2:7]1.[Br-].[H-].[Na+].[OH2:28].[CH3:29]N(C=O)C>>[CH3:1][C:2]1[C:14]([OH:15])=[C:13]([CH3:22])[C:12]([CH:23]=[CH2:29])=[C:11]2[C:3]=1[CH2:4][CH2:5][C:6]1([O:28]2)[CH2:7][CH2:8][CH2:9]1

Participants

6

Reactant 5

HCID 259Bromide ionHCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 86605488HCID 86605488, compound

Product 1

HCID 57803572HCID 57803572, compound

Procedure

A solution of 5,7-dimethyl-6-(tetrahydro-2H-pyran-2-yloxy)spiro[chroman-2,1′-cyclobutane]-8-carbaldehyde (1.5 g) and triphenylphosphinemethyl bromide (2.5 g) and sodium hydride (400 mg) in DMF (20 mL) was stirred at 40° C. for 5 h. After pouring it into water, it was extracted with ethyl acetate, and the organic layer was dried and evaporated. Then the residue was dissolved in MeOH with dil. HCl and it was stirred at room temperature for 30 min. The mixture was poured into water and extracted with ethyl acetate. The ethyl acetate was washed, dried, and evaporated. The residue was purified by silica gel column eluting with 10% ethyl acetate in hexane, giving 507.7 mg of 5,7-dimethyl-8-vinyl-3,4-dihydrospiro[chromene-2,1′-cyclobutan]-6-ol as a light brown oil.

Workup

  1. extractionwas extracted with ethyl acetate
  2. customthe organic layer was dried
  3. customevaporated
  4. dissolutionThen the residue was dissolved in MeOH with dil. HCl and it
  5. additionThe mixture was poured into water
  6. extractionextracted with ethyl acetate
  7. washThe ethyl acetate was washed
  8. customdried
  9. customevaporated
  10. customThe residue was purified by silica gel column
  11. washeluting with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-07657649cf93444b99d09c8b22fbaa50
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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