Triphenylphosphine → 1-Ethyl-1-[2-(trifluoromethyl)-2-propen-1-yl]-1,2,3,4-tetrahydronaphthalene

HRID 600746ノート

反応式

HRID 600746 の反応式
[CH2:1]([C:3](=[CH2:14])[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1I)[CH3:2].[F:15][C:16]([F:34])([F:33])[C:17](O)(CC1(C)C2C(=CC=CC=2)CCC1)[CH:18]=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Cu]I>[CH2:1]([C:3]1([CH2:14][C:17]([C:16]([F:34])([F:33])[F:15])=[CH2:18])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1)[CH3:2]

参加物

7

反応物 3

HCID 11776TriphenylphosphineHCID 116379981-(4-Ethyl-4-penten-1-yl)-2-iodobenzene2 回HCID 247491553,3,3-Trifluoro-2-hydroxy-2-[(1-methyl-1,2,3,4-tetrahydro-1-naphthalenyl)methyl]propanal2 回

生成物 1

HCID 116014351-Ethyl-1-[2-(trifluoromethyl)-2-propen-1-yl]-1,2,3,4-tetrahydronaphthalene収率 139.2%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

実験手順

1-(4-Ethyl-4-penten-1-yl)-2-iodobenzene (Intermediate 11) (1.1 g, 3.66 mmole), tributyl[1-(trifluoromethyl)ethenyl]stannane (Intermediate 3) (1.4 g, 3.64 mmole), triphenyl phosphine (188 mg, 0.717 mmole), palladium acetate (82 mg, 0.365 mmole) and copper(I) iodide (69 mg, 0.362 mmole) were dissolved in dry DMF (60 ml). The solution was degassed by evacuating and filling the flask with nitrogen four times. The solution was then immediately immersed in a 110° C. oil bath, left to react for 3.5 h, cooled to room temperature then partitioned between water (100 ml) and cyclohexane (100 ml). The layers were separated and the aqueous layer was extracted with further cyclohexane (100 ml). The combined extracts were dried over anhydrous sodium sulphate and evaporated and the residue was applied to a silica Solid Phase Extraction (SPE) cartridge. Elution with cyclohexane gave the title compound (1.36 g) containing some residual impurities. This was used without additional purification.

後処理

  1. customThe solution was degassed
  2. customby evacuating
  3. customwas then immediately immersed in a 110° C.
  4. waitleft
  5. customto react for 3.5 h
  6. customthen partitioned between water (100 ml) and cyclohexane (100 ml)
  7. customThe layers were separated
  8. extractionthe aqueous layer was extracted with further cyclohexane (100 ml)
  9. dry with materialThe combined extracts were dried over anhydrous sodium sulphate
  10. customevaporated
  11. extractionthe residue was applied to a silica Solid Phase Extraction (SPE) cartridge
  12. washElution with cyclohexane

出典と根拠

ORDレコード
ord-4b383e41778c4b7ab8abb4a9ef0a7cf7
出典データセット
uspto-grants-2011_03
特許番号
US07902224B2

反応ノート

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