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

HRID 1921892노트

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HRID 1921892 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매2회

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온도
100 °C

실험 절차

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

후처리

  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)

출처 및 근거

ORD 기록
ord-0ffa7ddc00b54485ae19303172bb6b80
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173704B2

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