Methanol → HCID 20211036, compound

HRID 1906887Notes

Reaction equation

HRID 1906887 reaction equation
[CH3:1][C:2]1[C:7]2[CH2:8][CH2:9][CH:10]([C:12](O)=[O:13])[O:11][C:6]=2[CH:5]=[C:4]([CH3:15])[CH:3]=1.B.S(C)C.CO>O1CCCC1>[CH3:1][C:2]1[C:7]2[CH2:8][CH2:9][CH:10]([CH2:12][OH:13])[O:11][C:6]=2[CH:5]=[C:4]([CH3:15])[CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 6331BoraneHCID 20211019HCID 20211019, compound

Product 1

HCID 20211036HCID 20211036, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred mixture of 109 parts of 3,4-dihydro-5,7-dimethyl-2H-1-benzopyran-2-carboxylic acid in 135 parts of tetrahydrofuran were added, during a period of 20 minutes, 292 parts of a solution of borane, compound with thiobismethane, in tetrahydrofuran 2M (foaming). The whole was stirred and refluxed for 2 hours. The mixture was decomposed by the addition of 24 parts of methanol. After stirring for 10 minutes at reflux temperature, the solvent was distilled off. Water was added to the residue. Concentrate hydrochloric acid was added and the product was extracted with 1,1'-oxybisethane. The organic layer was washed with water and sodium chloride, dried, filtered and evaporated, yielding 97.5 parts (96%) of 3,4-dihydro-5,7-dimethyl-2H-1-benzopyran-2-methanol as an oily residue (intermediate 16).

Workup

  1. additionwere added, during a period of 20 minutes
  2. temperaturerefluxed for 2 hours
  3. stirringAfter stirring for 10 minutes
  4. temperatureat reflux temperature
  5. distillationthe solvent was distilled off
  6. additionWater was added to the residue
  7. additionConcentrate hydrochloric acid was added
  8. extractionthe product was extracted with 1,1'-oxybisethane
  9. washThe organic layer was washed with water and sodium chloride
  10. customdried
  11. filtrationfiltered
  12. customevaporated

Sources & evidence

ORD record
ord-752ff23065fc497792502a2b1ef3d82b
Source dataset
uspto-grants-1987_03
Patent number
US04654362

Reaction notes

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