Ammonium Chloride → alpha-Trimethylsilylethynyl-4,4-dimethyl-6-thiochromanmethanol

HRID 840448Notes

Reaction equation

HRID 840448 reaction equation
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].C([Li])CCC.[CH3:12][C:13]1([CH3:25])[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([CH:23]=[O:24])[CH:21]=2)[S:16][CH2:15][CH2:14]1.[Cl-].[NH4+]>C1COCC1>[CH3:1][Si:2]([CH3:4])([CH3:3])[C:5]#[C:6][CH:15]1[CH2:14][C:13]([CH3:12])([CH3:25])[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([CH2:23][OH:24])[CH:21]=2)[S:16]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 66111TrimethylsilylacetyleneHCID 152843084,4-dimethyl-3,4-dihydro-2H-thiochromene-6-carbaldehydeHCID 178418339Butyllithium

Product 1

HCID 22361487alpha-Trimethylsilylethynyl-4,4-dimethyl-6-thiochromanmethanolYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3 ml (21.3 mmol) of trimethylsilylacetylene and 50 ml of THF were introduced into a three-necked flask. A solution of 8.6 ml (21.3 mmol) of n-butyllithium (2.5M in hexane) was added dropwise at −78° C. under a stream of nitrogen and the reaction mixture was permitted to heat to room temperature. This solution was introduced dropwise into a solution of 4 g (19.4 mmol) of 4,4-dimethyl-6-thiochromancarboxaldehyde in 50 ml of THF at −78° C. The reaction mixture was permitted to heat to room temperature, was poured into an aqueous ammonium chloride solution and extracted with ethyl ether. The organic phase was separated by settling, dried over magnesium sulfate and evaporated. 5.9 g (100%) of the expected alcohol were obtained in the form of a yellow oil.

Workup

  1. temperatureto heat to room temperature
  2. extractionextracted with ethyl ether
  3. customThe organic phase was separated
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-22ca85786dc54007b7021d2f324c09eb
Source dataset
uspto-grants-2002_04
Patent number
US06368608B1

Reaction notes

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