Water → HCID 22619442, compound

HRID 840463Notes

Reaction equation

HRID 840463 reaction equation
[CH3:1][C:2]1([CH3:14])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[CH:13])[CH:10]=2)[S:5][CH2:4][CH2:3]1.C([Li])CCC.[C:20]([C:23]1[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=1)([OH:22])=[O:21].O>C1COCC1>[OH:28][CH:27]([C:26]1[CH:25]=[CH:24][C:23]([C:20]([OH:22])=[O:21])=[CH:30][CH:29]=1)[C:13]#[C:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[S:5][CH2:4][CH2:3][C:2]2([CH3:14])[CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 120884-Formylbenzoic acidHCID 109325396-Ethynyl-4,4-dimethylthiochromanHCID 178418339Butyllithium

Product 1

HCID 22619442HCID 22619442, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2 g (9.9 mmol) of (4,4-dimethylthiochroman-6-yl) acetylene and 25 ml of THF were introduced into a three-necked flask under a stream of nitrogen, 4 ml (9.9 mmol) of an n-butyllithium solution (2.5M in hexane) were added dropwise at −50° C. and stirring was carried out for 30 min. A solution of 743 mg (4.9 mmol) of 4-carboxybenzaldehyde in 25 ml of THF was then added and stirring was carried out at room temperature for one hour. The reaction mixture was poured into water and extracted with ethyl ether. The organic phase was separated by settling, dried over magnesium sulfate and evaporated. The residue was recrystallized from diisopropyl ether. After filtration, 730 mg (42%) of the expected acid, with a melting point of 168°-169° C., were obtained.

Workup

  1. additionwere added dropwise at −50° C.
  2. stirringstirring
  3. waitwas carried out at room temperature for one hour
  4. extractionextracted with ethyl ether
  5. customThe organic phase was separated
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe residue was recrystallized from diisopropyl ether
  9. filtrationAfter filtration, 730 mg (42%) of the expected acid
  10. customwith a melting point of 168°-169° C., were obtained

Sources & evidence

ORD record
ord-5d670cd7215a4e4589b9f73b9b789c08
Source dataset
uspto-grants-2002_04
Patent number
US06368608B1

Reaction notes

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