Ammonium Chloride → alpha-Trimethylsilylethynyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenemethanol

HRID 861773Notes

Reaction equation

HRID 861773 reaction equation
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].C([Li])CCC.[CH3:12][C:13]1([CH3:27])[CH2:22][CH2:21][C:20]([CH3:24])([CH3:23])[C:19]2[CH:18]=[C:17]([CH:25]=[O:26])[CH:16]=[CH:15][C:14]1=2.[Cl-].[NH4+]>C1COCC1>[CH3:1][Si:2]([CH3:4])([CH3:3])[C:5]#[C:6][C:18]1[C:19]2[C:20]([CH3:23])([CH3:24])[CH2:21][CH2:22][C:13]([CH3:27])([CH3:12])[C:14]=2[CH:15]=[CH:16][C:17]=1[CH2:25][OH:26]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 66111TrimethylsilylacetyleneHCID 104208875,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-2-naphthalenecarbaldehydeHCID 178418339Butyllithium

Product 1

HCID 86752031alpha-Trimethylsilylethynyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenemethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

17.13 ml (0.121 mol) of trimethylsilylacetylene and 100 ml of THF were introduced into a three-necked flask. A solution of 48.5 ml (0.121 mol) of n-butyllithium (2.5M in hexane) was added dropwise at -78° C. under a stream of nitrogen and the mixture was permitted to heat to room temperature. This solution was introduced dropwise into a solution of 23.8 g (0.11 mol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenecarboxaldehyde in 100 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 was extracted with ethyl ether. The organic phase was separated by settling, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a silica column eluted with a mixture of dichloromethane and hexane (50/50). After evaporating the solvents, 29.9 g (86%) of the expected alcohol were recovered in the form of a yellow oil.

Workup

  1. temperatureto heat to room temperature
  2. extractionwas extracted with ethyl ether
  3. customThe organic phase was separated
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue obtained
  7. customwas purified by chromatography on a silica column
  8. washeluted with a mixture of dichloromethane and hexane (50/50)
  9. customAfter evaporating the solvents, 29.9 g (86%) of the expected alcohol
  10. customwere recovered in the form of a yellow oil

Sources & evidence

ORD record
ord-3df848923e264fb881918969429fc3f5
Source dataset
uspto-grants-1998_02
Patent number
US05716624

Reaction notes

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