Citric Acid → HCID 57508884, compound

HRID 1013438Notes

Reaction equation

HRID 1013438 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:13][CH2:12][C:5]2=[C:6]([C:9]([OH:11])=[O:10])[S:7][CH:8]=[C:4]2[CH2:3]1.[C:15]([Li])(C)(C)C.CI.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.O>[CH3:15][C:8]1[S:7][C:6]([C:9]([OH:11])=[O:10])=[C:5]2[CH2:12][CH2:13][C:2]([CH3:14])([CH3:1])[CH2:3][C:4]=12

Participants

7

Reactant 4

HCID 311Citric AcidHCID 6328Methyl iodideHCID 57508882HCID 57508882, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 57508884HCID 57508884, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

At −78° C. a solution of 5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid (5 g, 23.8 mmol) in THF is treated with tert-butyllithium (41 mL, 1.5 M in pentane). The mixture is stirred at −78° C. for 15 min before methyliodide (17.1 g, 120 mmol) is added dropwise. Stirring is continued at −78° C. for 30 min. The mixture is warmed to rt, diluted with water (400 mL), acidified with 10% aq. citric acid solution and extracted three times with EA. The combined organic extracts are dried over MgSO4 and evaporated. The remaining solid is suspended in heptane/diethyl ether, filtered and dried under HV to give 3,5,5-trimethyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid (4.01 g) as a beige powder; LC-MS: tR=0.97 min; [M+1]=225.13; 1H NMR (D6-DMSO): δ 12.49 (s br, 1H), 2.87 (t, J=6.7 Hz, 2H), 2.26 (s, 5H), 1.45 (t, J=6.7 Hz, 2H), 0.91 (s, 6H).

Workup

  1. additionis added dropwise
  2. extractionextracted three times with EA
  3. dry with materialThe combined organic extracts are dried over MgSO4
  4. customevaporated
  5. filtrationfiltered
  6. customdried under HV

Sources & evidence

ORD record
ord-bcea0cf64e224adb9c1fd1352be227b9
Source dataset
uspto-grants-2011_07
Patent number
US07981924B2

Reaction notes

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