Formic Acid → 4-(4-Cyanophenyl)-2-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)butanoic acid

HRID 1921892ノート

反応式

HRID 1921892 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([CH2:24][C:25]2[CH:30]=[C:29]([F:31])[C:28]([O:32][Si:33]([CH:40]([CH3:42])[CH3:41])([CH:37]([CH3:39])[CH3:38])[CH:34]([CH3:36])[CH3:35])=[C:27]([F:43])[CH:26]=2)(C(OCC=C)=O)[C:12]([O:14]CC=C)=[O:13])=[CH:5][CH:4]=1)#[N:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.C(O)=O>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH:11]([CH2:24][C:25]2[CH:26]=[C:27]([F:43])[C:28]([O:32][Si:33]([CH:34]([CH3:36])[CH3:35])([CH:37]([CH3:39])[CH3:38])[CH:40]([CH3:41])[CH3:42])=[C:29]([F:31])[CH:30]=2)[C:12]([OH:14])=[O:13])=[CH:5][CH:4]=1)#[N:2]

参加物

7

反応物 4

HCID 284Formic AcidHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 57971937Diallyl 2-[2-(4-cyanophenyl)ethyl]-2-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)malonate

生成物 1

HCID 579718994-(4-Cyanophenyl)-2-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)butanoic acid

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒2 回

反応条件

温度
100 °C

実験手順

4720 mg (7.72 mmol) of diallyl 2-[2-(4-cyanophenyl)ethyl]-2-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)malonate, 34.6 mg (0.15 mmol) of palladium(II) acetate and 141.6 mg (0.54 mmol) of triphenylphosphine are stirred in 180 ml of dioxane under argon. Then a solution of 2576 mg (25.60 mmol) of triethylamine and 887.7 mg (19.29 mmol) of formic acid in 90 ml of dioxane is added dropwise, and the mixture is heated at 100° C. for 2 h. The cooled mixture is concentrated and the crude product is chromatographed on silica gel (mobile phase: cyclohexane/ethyl acetate 9:1→2:1→1:1). 3682 mg (97.9% of theory) of the title compound are obtained

後処理

  1. concentrationThe cooled mixture is concentrated
  2. customthe crude product is chromatographed on silica gel (mobile phase: cyclohexane/ethyl acetate 9:1→2:1→1:1)

出典と根拠

ORDレコード
ord-0ffa7ddc00b54485ae19303172bb6b80
出典データセット
uspto-grants-2012_05
特許番号
US08173704B2

反応ノート

読み込み中…