Potassium Carbonate → HCID 69935910, compound

HRID 1265261Notes

Reaction equation

HRID 1265261 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:12]2[C:21]([OH:22])=[CH:20][C:19]3[C:18]([CH3:24])([CH3:23])[CH2:17][CH2:16][C:15]([CH3:26])([CH3:25])[C:14]=3[CH:13]=2)=[O:11])=[CH:6][CH:5]=1.C([O-])([O-])=O.[K+].[K+].[C:34]([C:38]1[CH:45]=[CH:44][C:41]([CH2:42]Br)=[CH:40][CH:39]=1)([CH3:37])([CH3:36])[CH3:35]>CC(C)=O>[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:12]2[C:21]([O:22][CH2:42][C:41]3[CH:44]=[CH:45][C:38]([C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:39][CH:40]=3)=[CH:20][C:19]3[C:18]([CH3:23])([CH3:24])[CH2:17][CH2:16][C:15]([CH3:26])([CH3:25])[C:14]=3[CH:13]=2)=[O:11])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzeneHCID 10021814HCID 10021814, compound

Product 1

HCID 69935910HCID 69935910, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of the 4-[(3-hydroxy-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)carbonyl]benzoic acid methyl ester (from Example 7; 225 mg, 0.61 mmol) in acetone (3 mL) was stirred with K2CO3 (1.0 mmol) at room temperature for one hour. The yellow solution was treated with a solution of 4-t-butylbenzylbromide (168 mg, 0.74 mmol) and allowed to stir for 10 h. The reaction was quenched with saturated aqueous NH4Cl. The aqueous solution was extracted 3 times with EtOAc; the organic layers were combined, and washed with water (2×) and brine. The organic solution was dried (NaSO4), filtered, and concentrated. Purification by cyrstallization (CH2Cl2/hexanes) gave 4-[(3-(4-t-butylbenzyloxy)-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)carbonyl]benzoic acid methyl ester 298 mg (95%) as a white solid: mp 168-169.5° C; 1H NMR (400 MHz, CDCl3) δ 8.04 (1/2ABq, J=8.5 Hz, 2H, ArH), 7.81 (1/2ABq, J=8.5 Hz, 2H, ArH), 7.44 (s, 1H, ArH), 7.19 (1/2ABq, J=8.2 Hz, 2H, ArH), 6.89 (s, 1H, ArH), 6.87 (1/2ABq, J=8.4 Hz, 2H, ArH), 4.89 (s, 2H, OCH2), 3.94 (s, 3H, OCH3), 1.69 (m, 4H, 2CH2), 1.28 (s, 6H, 2CH3), 1.26 (s, 6H, 2CH3), 1.25 (s, 9H, 3CH3).

Workup

  1. customThe reaction was quenched with saturated aqueous NH4Cl
  2. extractionThe aqueous solution was extracted 3 times with EtOAc
  3. washwashed with water (2×) and brine
  4. dry with materialThe organic solution was dried (NaSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by cyrstallization (CH2Cl2/hexanes)

Sources & evidence

ORD record
ord-d0de991e105a43d7811c2e28cf73e304
Source dataset
uspto-grants-2003_04
Patent number
US06545049B1

Reaction notes

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