Hydrochloric Acid → HCID 18357338, compound

HRID 563875Notes

Reaction equation

HRID 563875 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][CH:9](O)[CH2:8][CH:7]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH:21]([NH:24][CH:25]([CH3:27])[CH3:26])([CH3:23])[CH3:22].[H][H].[ClH:30]>C1(C)C=CC=CC=1.[OH-].[OH-].[Pd+2]>[ClH:30].[CH:21]([N:24]([CH:25]([CH3:27])[CH3:26])[CH2:9][CH2:8][CH:7]([C:6]1[CH:5]=[C:4]([CH2:3][CH2:2][OH:1])[CH:13]=[CH:12][C:11]=1[OH:10])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:23])[CH3:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 580035013,4-Dihydro-2-hydroxy-4-phenyl-2H-1-benzopyran-6-ethanolHCID 178418361HCID 178418361, compound

Product 1

HCID 18357338HCID 18357338, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 6-(2-hydroxy-ethyl)-4-phenyl-chroman-2-ol (Example 7, 30 g, 111 mmol, 1 equiv), diisopropylamine (33.7 g, 333 mmol, 3 eq) and palladium hydroxide on carbon [50% wet catalyst (50% by weight is water), 6 g, 0.2 equiv] in toluene (120 mL) was hydrogenated at 621×103 Nm−2 (90 psi) hydrogen pressure at 110° C. The reaction mixture was cooled to room temperature and filtered through arbocel and evaporated under reduced pressure. The resulting oil was dissolved in acetonitrile (200 mL) and concentrated hydrochloric acid (11.6 mL, 1.05 equiv) was added. The mixture was distilled at ambient pressure, removing approximately 100 mL of acetonitrile, and the distilled solvent replaced with fresh acetonitrile. The mixture was allowed to cool and crystallise overnight. The product was filtered and washed with a small portion of acetonitrile and dried overnight in vacuo at 50° C. to give the title compounds as a white solid (26.7 g, 68.1 mmol, 61%).

Workup

  1. filtrationfiltered through arbocel
  2. customevaporated under reduced pressure
  3. dissolutionThe resulting oil was dissolved in acetonitrile (200 mL)
  4. distillationThe mixture was distilled at ambient pressure
  5. customremoving approximately 100 mL of acetonitrile
  6. temperatureto cool
  7. customcrystallise overnight
  8. filtrationThe product was filtered
  9. washwashed with a small portion of acetonitrile
  10. customdried overnight in vacuo at 50° C.

Sources & evidence

ORD record
ord-732f3b33d03c4e66b04b4a31767e0a71
Source dataset
uspto-grants-2011_11
Patent number
US08067594B2

Reaction notes

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