Hydrochloric Acid → HCID 11992476, compound

HRID 2241033Notes

Reaction equation

HRID 2241033 reaction equation
C([O:3][C:4](=O)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[C:14]2[CH2:19][C:18]([CH3:21])([CH3:20])[CH2:17][C:16]([CH3:23])([CH3:22])[CH2:15]2)=[CH:9][CH:8]=1)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].Cl>C1COCC1>[F:30][C:27]1[CH:26]=[CH:25][C:24]([C:13](=[C:14]2[CH2:15][C:16]([CH3:23])([CH3:22])[CH2:17][C:18]([CH3:21])([CH3:20])[CH2:19]2)[C:10]2[CH:11]=[CH:12][C:7]([O:6][CH2:5][CH2:4][OH:3])=[CH:8][CH:9]=2)=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 86646615HCID 86646615, compound

Product 1

HCID 11992476HCID 11992476, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl({4-[(4-fluorophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}oxy)acetate 10 (0.580 g, 1.336 mmol) in anhydrous THF (25 mL) was added LiAlH4 (3.4 mL, 3.42 mmol, 1.0 M solution in THF) drop-wise under N2 atmosphere at room temperature. The resultant solution was stirred at RT for 0.5 h. The reaction mixture was quenched with EtOAc (10 mL) and continued the stirring for an additional 10 min. Reaction mixture was poured into 15% aqueous HCl (50 mL) and then extracted with EtOAc (4×30 mL). The combined organic layer was washed with brine (1×30 mL), dried (Na2SO4), and concentrated under reduced pressure to afford the crude product. The product was purified by silica gel column chromatography using hexanes: EtOAc (19:1 to 4:1) as an eluent to afford 0.41 g (79%) of the title compound (15) as white foam. 1H NMR (400 MHz, DMSO-d6): δ 7.16-7.06 (m, 4H), 7.03 (d, J=8.4 Hz, 2H), 6.84 (d, J=6.4 Hz, 2H), 4.83 (t, J=5.6 Hz, 1H), 3.92 (t, J=5.2 Hz, 2H), 3.67 (q, J1=10.8 Hz, J2=5.2 Hz, 2H), 1.90 (s, 2H), 1.86 (s, 2H), 1.24 (s, 2H), 0.87 (s, 6H), 0.87 (6H). LCMS (APCI): m/z 405 (M+Na)+.

Workup

  1. customThe reaction mixture was quenched with EtOAc (10 mL)
  2. customstirring for an additional 10 min
  3. customReaction mixture
  4. extractionextracted with EtOAc (4×30 mL)
  5. washThe combined organic layer was washed with brine (1×30 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customto afford the crude product
  9. customThe product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e7cb82a0d5f2448386fdd689d7f15a82
Source dataset
uspto-grants-2010_05
Patent number
US07723393B2

Reaction notes

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