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

HRID 840452ノート

反応式

HRID 840452 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7c72b7e880dd4a138605a042e0abbdd1
出典データセット
uspto-grants-2002_04
特許番号
US06368608B1

反応ノート

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