Triethylamine → HCID 11302995, compound

HRID 2100100Notes

Reaction equation

HRID 2100100 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[C:18]2[CH2:23][C:22]([CH3:25])([CH3:24])[CH2:21][C:20]([CH3:27])([CH3:26])[CH2:19]2)[C:9]2[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.CC[N:30](CC)CC.ClC(OCC)=O.[NH4+].[OH-].[NH4+].[Cl-]>C1COCC1>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[C:18]2[CH2:23][C:22]([CH3:25])([CH3:24])[CH2:21][C:20]([CH3:27])([CH3:26])[CH2:19]2)[C:9]2[CH:17]=[CH:16][C:12]([C:13]([NH2:30])=[O:14])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 11199337843661-24-5

Product 1

HCID 11302995HCID 11302995, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold (−15° C.) solution of 4-[(4-hydroxyphenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]benzoic acid (0.100 g, 0.274 mmol) (26) in THF were added Et3N (0.042 mL, 0.302 mmol) and ethyl chloroformate (0.029 mL, 0.302 mmol) sequentially. The resultant solution was stirred at that temperature for 0.5 h. An aqueous 28% NH4OH solution was added slowly to the above mixture at −15° C. and stirred the resultant mixture at room temperature for 15 h. Reaction mixture was poured into sat. NH4Cl solution (30 mL) and then extracted with EtOAc (2×40 mL). The combined organic layer washed with brine (1×25 mL), dried (Na2SO4), and concentrated under reduced pressure to afford the crude product. The product was purified by SiO2 column chromatography using CHCl3 and MeOH (100:00 to 9:1) as an eluent to afford 0.035 g (35%) of the title compound (95) as white crystalline solid. Around 25 mg of starting material was also recovered from this reaction. mp 209° C.-210° C. 1H NMR (400 MHz, DMSO-d6): δ 9.29 (s, 1H), 7.87 (s, 1H), 7.75 (d, J=8.0 Hz, 2H), 7.27 (s, 1H), 7.15 (d, J=8.0 Hz, 2H), 6.92 (d, J=8.4 Hz, 2H), 6.65 (d, J=8.4 Hz, 2H), 1.91 (s, 2H), 1.85 (s, 2H), 1.24 (s, 2H), 0.87 (s, 6H), 0.85 (s, 6H). LCMS (ESI): m/z 362.31 (M−H)−.

Workup

  1. customReaction mixture
  2. extractionextracted with EtOAc (2×40 mL)
  3. washThe combined organic layer washed with brine (1×25 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customto afford the crude product
  7. customThe product was purified by SiO2 column chromatography

Sources & evidence

ORD record
ord-4e1ac8aedddb480c9e58ecfb97b5a2d7
Source dataset
uspto-grants-2009_08
Patent number
US07569601B2

Reaction notes

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