Hydrochloric Acid → HCID 86587150, compound

HRID 897065Notes

Reaction equation

HRID 897065 reaction equation
[OH-].[Na+].[CH3:3][C:4]([C:11]#[C:12][S:13]([C:16]1[CH:25]=[CH:24][C:23]2[C:22]([CH3:27])([CH3:26])[CH2:21][CH2:20][C:19]([CH3:29])([CH3:28])[C:18]=2[CH:17]=1)(=[O:15])=[O:14])=[CH:5][C:6]([O:8]CC)=[O:7].C(OCC)C.O.Cl>O.C1COCC1>[CH3:3][C:4]([C:11]#[C:12][S:13]([C:16]1[CH:25]=[CH:24][C:23]2[C:22]([CH3:27])([CH3:26])[CH2:21][CH2:20][C:19]([CH3:29])([CH3:28])[C:18]=2[CH:17]=1)(=[O:15])=[O:14])=[CH:5][C:6]([OH:8])=[O:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21584184Diethylether waterHCID 73884447HCID 73884447, compound

Product 1

HCID 86587150HCID 86587150, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

NaOH (100 mg, 2.5 mmol) in water is added to a solution of ethyl 3-methyl-5-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ylsulphonyl)pent-2-en-4-ynoate (605 mg, 1.7 mmol) in 15 ml of THF. The medium is then refluxed for 6 h. Next, it is 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 crystallized from methanol.

Workup

  1. temperatureThe medium is then refluxed for 6 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 crystallized from methanol

Sources & evidence

ORD record
ord-b2dfb179585c4b1ca16d964f1de1db7c
Source dataset
uspto-grants-2005_07
Patent number
US06921777B2

Reaction notes

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