HCID 90031358, compound → HCID 90057790, compound

HRID 1771271Notes

Reaction equation

HRID 1771271 reaction equation
[CH2:1]([C:4]1[CH:11]=[C:10]([F:12])[CH:9]=[C:6]([CH:7]=[O:8])[C:5]=1[OH:13])[CH:2]=[CH2:3]>C1(SC2C=CC=CC=2)C=CC=CC=1.CCOC(C)=O>[F:12][C:10]1[CH:11]=[C:4]([CH2:1][CH2:2][CH3:3])[C:5]([OH:13])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

4

Reactant 1

HCID 90031358HCID 90031358, compound2×

Product 1

HCID 90057790HCID 90057790, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 8766Diphenyl sulfideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a round-bottom flask were added aldehyde 47d (1.10 g, 6.11 mmol, 1.0 equiv.), 5% Pd/C (220 mg, 20 wt % of 47d), diphenyl sulfide (10 μL, 0.061 mmol, 0.010 equiv.), and EtOAc (25 mL, 0.25 M). The reaction mixture was stirred overnight at room temperature under an atmosphere of H2 (balloon pressure). The reaction mixture was filtered through Celite and washed thoroughly with EtOAc. The filtrate was concentrated to afford aldehyde 47e (991 mg, 89.3%) as a yellow oil. 1H-NMR (500 MHz, CDCl3) δ 11.06 (br s, 1H), 9.80 (s, 1H), 7.12 (dd, 1H, J=3.0, 9.0 Hz), 7.06 (dd, 1H, J=3.0, 7.5 Hz), 2.62 (t, 2H, J=7.5 Hz), 1.63 (sext, 2H, J=7.5 Hz), 0.96 (t, 3H, J=7.5 Hz). 13C-NMR (125 MHz, CDCl3) δ 195.9 (d, JC-F=2.5 Hz), 156.3 (d, JC-F=1.0 Hz), 155.5 (d, JC-F=238.1 Hz), 133.9 (d, JC-F=6.3 Hz), 124.7 (d, JC-F=23.1 Hz), 119.6 (d, JC-F=6.5 Hz), 115.4 (d, JC-F=22.4 Hz), 31.2, 22.4, 14.0. 19F-NMR (470 MHz, CDCl3) δ −127.3. HRMS (EI): 182.07392 (M+); calcd. for C10H11FO2: 182.07431.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washwashed thoroughly with EtOAc
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-2d17feaeadbc4e3ca179efa7c5333f59
Source dataset
uspto-grants-2016_02
Patent number
US09249116B2

Reaction notes

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