Acetic Acid → HCID 9883524, compound

HRID 1934512Notes

Reaction equation

HRID 1934512 reaction equation
[CH:1]1([CH:7]([CH2:18][C:19]([C:21]2[O:22][CH:23]=[CH:24][CH:25]=2)=O)[CH2:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=2)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC(O)=O.C[N:31](C)C=O>>[CH:1]1([C:7]2[CH:18]=[C:19]([C:21]3[O:22][CH:23]=[CH:24][CH:25]=3)[N:31]=[C:9]([C:11]3[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=3)[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 18679586HCID 18679586, compound

Product 1

HCID 9883524HCID 9883524, compound

Conditions

Temperature
100 °C

Procedure

A mixture of 3-cyclohexyl-1-(3-hydroxyphenyl)-5-(furan-2-yl)-1,5-pentanedione on Wang resin (2.7 g, 1.90 mmol), NH4OAc (1.7 g), and AcOH (1.7 mL) in dimethylformamide (30 mL) was heated at 100° C. for 18 h. The resin was filtered, and washed with dimethylformamide (×2) and alternating MeOH and CH2Cl2 (×5), and dried under high vacuum overnight. The dried resin was treated with 50% TFA/CH2Cl2 (15 mL) for 1 h. After filtration of the reaction mixture, the filtrate was concentrated to dryness. The residue was repeatedly dissolved in CH2Cl2 (10 mL) and concentrated to remove traces of TFA. Purification by flash chromatography gave 3-(4-cyclohexyl-6-furan-2-yl-pyridin-2-yl)-phenol; 1H NMR (DMSO-d6) d 1.42 (m, 4H), 1.71 (m, 2H), 1.85 (m, 4H), 2.64 (m, 1H), 6.67 (dd, J=3.3, 1.5 Hz, 1 H), 6.85 (dd, J=8.1, 1.8 Hz, 1H); 7.18 (d, J=3.3 Hz, 1H), 7.29 (m, 1H), 7.57 (m, 3H), 7.63 (s, 1H), 7.85 (s, 1H), 9.54 (s, 1H); IR (KBr) 1607 cm−1; MS [M+H]+ m/z 320. Anal. calcd for C21H21NO2.0.6 C4H8O2: C, 75.52; H, 6.94; N, 3.77; Found: C, 75.72; H, 6.72; N, 3.55.

Workup

  1. filtrationThe resin was filtered
  2. washwashed with dimethylformamide (×2)
  3. customdried under high vacuum overnight
  4. additionThe dried resin was treated with 50% TFA/CH2Cl2 (15 mL) for 1 h
  5. filtrationAfter filtration of the reaction mixture
  6. concentrationthe filtrate was concentrated to dryness
  7. dissolutionThe residue was repeatedly dissolved in CH2Cl2 (10 mL)
  8. concentrationconcentrated
  9. customto remove traces of TFA
  10. customPurification by flash chromatography

Sources & evidence

ORD record
ord-49b6cefe7ba84186ac28a877eb39d664
Source dataset
uspto-grants-2002_05
Patent number
US06384057B1

Reaction notes

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