Hydrochloric Acid → HCID 9950967, compound

HRID 2305603Notes

Reaction equation

HRID 2305603 reaction equation
[CH3:1][C:2]1([CH3:27])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([S:14][C:15]#[C:16][C:17]3[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[CH:19][CH:18]=3)[CH:5]=[CH:4][C:3]1=2.[OH-].[Li+].CCOCC.O.Cl>C1COCC1>[CH3:1][C:2]1([CH3:27])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([S:14][C:15]#[C:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[CH:25][CH:26]=3)[CH:5]=[CH:4][C:3]1=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 15406546HCID 15406546, compoundHCID 21584184Diethylether water

Product 1

HCID 9950967HCID 9950967, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthylsulphanylethynyl)benzoate (590 mg, 1.6 mmol) and of lithium hydroxide (383 mg, 9.3 mmol) in THF is refluxed for 24 hours. The reaction mixture is poured into an Et2O/water mixture, acidified to pH 1 with concentrated hydrochloric acid solution, and extracted once with ethyl ether. After separation of the phases by settling, the organic phase is washed twice with water, dried over magnesium sulphate and concentrated on a rotary evaporator under vacuum at 40° C. The solid obtained is crystallized from heptane and 440 mg (77%) of a white solid are obtained. m.p. (melting point)=193.5° C.

Workup

  1. extractionextracted once with ethyl ether
  2. customAfter separation of the phases
  3. washthe organic phase is washed twice with water
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated on a rotary evaporator under vacuum at 40° C
  6. customThe solid obtained
  7. customis crystallized from heptane and 440 mg (77%) of a white solid
  8. customare obtained
  9. customm.p. (melting point)=193.5° C.

Sources & evidence

ORD record
ord-1295e72d15624bdc8cef4a71bfc453bc
Source dataset
uspto-grants-2002_08
Patent number
US06441010B2

Reaction notes

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