Ethyl Acetate → HCID 86669890, compound

HRID 1506383Notes

Reaction equation

HRID 1506383 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:14][CH2:15][C:16]3[O:17][C:18]4[CH:28]=[CH:27][C:26]5[C:21](=[CH:22][CH:23]=[C:24]([CH:29]([OH:32])CO)[CH:25]=5)[C:19]=4[N:20]=3)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.I([O-])(=O)(=O)=O.[Na+].C(OCC)(=O)C>CO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:14][CH2:15][C:16]3[O:17][C:18]4[CH:28]=[CH:27][C:26]5[C:21](=[CH:22][CH:23]=[C:24]([CH:29]=[O:32])[CH:25]=5)[C:19]=4[N:20]=3)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 23667635Sodium periodateHCID 67170954HCID 67170954, compound

Product 1

HCID 86669890HCID 86669890, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-(2-(2-(1-(4-fluorophenyl)cyclohexyl)ethyl)naphtho[1,2-d]oxazol-7-yl)ethane-1,2-diol (Preparation 42D, 0.051 g, 0.117 mmol) in methanol (1 mL) at 0° C. was added a solution of sodium periodate (0.038 g, 0.176 mmol) in water (1.000 mL) dropwise and the mixture was stirred for 30 mins at the same temp. Next, about 5 mL of ethyl acetate was added and the mixture was stirred for an addition 1 hr at 0-10° C. The mixture was extracted with EtOAc, washed with brine, dried over sodium sulfate, and evaporated to give the desired 2-(2-(1-(4-fluorophenyl)cyclohexyl)ethyl)naphtho[1,2-d]oxazole-7-carbaldehyde as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 10.17 (1H, s), 8.51 (1H, d, J=8.58 Hz), 8.44 (1H, s), 8.09 (1H, dd, J=8.58, 1.32 Hz), 7.89 (1H, d, J=9.02 Hz), 7.68 (1H, d, J=9.02 Hz), 7.35 (2H, dd, J=9.02, 5.28 Hz), 7.02 (2H, t, J=8.69 Hz), 2.66-2.72 (2H, m), 2.15-2.22 (2H, m), 1.17-1.92 (10H, m).

Workup

  1. stirringthe mixture was stirred for an addition 1 hr at 0-10° C
  2. extractionThe mixture was extracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-d5bcae93893e49dbada2c1268e116fdb
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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