Hydrochloric Acid → 3-Methyl-5-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-ylsulphonyl)pent-2-en-4-ynoic Acid

HRID 1278839Notes

Reaction equation

HRID 1278839 reaction equation
[OH-].[Na+].[CH3:3][C:4]([C:11]#[C:12][S:13]([C:16]1[C:25]([CH3:26])=[CH:24][C:23]2[C:22]([CH3:28])([CH3:27])[CH2:21][CH2:20][C:19]([CH3:30])([CH3:29])[C:18]=2[CH:17]=1)(=[O:15])=[O:14])=[CH:5][C:6]([O:8]CC)=[O:7].C(OCC)C.O.Cl>C1COCC1>[CH3:3][C:4]([C:11]#[C:12][S:13]([C:16]1[C:25]([CH3:26])=[CH:24][C:23]2[C:22]([CH3:28])([CH3:27])[CH2:21][CH2:20][C:19]([CH3:30])([CH3:29])[C:18]=2[CH:17]=1)(=[O:15])=[O:14])=[CH:5][C:6]([OH:8])=[O:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21584184Diethylether waterHCID 73884431Ethyl 3-methyl-5-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-ylsulphonyl)pent-2-en-4-ynoate

Product 1

HCID 738844293-Methyl-5-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-ylsulphonyl)pent-2-en-4-ynoic Acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydroxide (400 mg, 10 mmol) is added to a solution of ethyl 3-methyl-5-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-ylsulphonyl)pent-2-en-4-ynoate (400 mg, 1.6 mmol) in 15 ml of THF. The medium is refluxed for 4 h. It is then poured into an ethyl ether/water mixture, acidified to pH 1 with concentrated hydrochloric acid solution and extracted with ethyl ether. After separation of the phases by settling, the organic phase is washed twice with water, dried over anhydrous magnesium sulphate and concentrated on a rotary evaporator under vacuum at 40° C. The residue is then triturated from heptane, after which it is filtered.

Workup

  1. temperatureThe medium is refluxed for 4 h
  2. extractionextracted with ethyl ether
  3. customAfter separation of the phases
  4. washthe organic phase is washed twice with water
  5. dry with materialdried over anhydrous magnesium sulphate
  6. concentrationconcentrated on a rotary evaporator under vacuum at 40° C
  7. customThe residue is then triturated from heptane
  8. filtrationafter which it is filtered

Sources & evidence

ORD record
ord-b5b0ab3ad8e745668a3f0733ed6e3545
Source dataset
uspto-grants-2002_09
Patent number
US06444709B1

Reaction notes

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