Potassium Carbonate → 4'-Ethynyl-2-(trifluoromethyl)biphenyl

HRID 710443

반응식

HRID 710443 반응식
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][CH:10]=1.[C:19]([O-])([O-])=O.[K+].[K+].[N+](=C(P(=O)(OC)OC)C(=O)C)=[N-]>CO>[C:15]([C:12]1[CH:13]=[CH:14][C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[C:2]([F:18])([F:17])[F:1])=[CH:10][CH:11]=1)#[CH:19]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 13926532'-TrifluoroMethyl-Biphenyl-4-CarbaldehydeHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

생성물 1

HCID 866618064'-Ethynyl-2-(trifluoromethyl)biphenyl수율 85.4%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

To a stirred suspension of the product of Example 36, Step A, (0.21 g, 1 mmol) and K2CO3 (0.166 g, 1.1 mmol) in anhydrous MeOH (5 mL) was added a solution of dimethyl 1-diazo-2-oxopropylphosphonate (0.212 g, 1.1 mmol) in anhydrous MeOH (1 ml) and the mixture was stirred overnight at room temperature. The solvent was evaporated to dryness and the residue was diluted to 50 ml with EtOAc and washed with H2O. The organic layer was separated, dried over MgSO4, and filtered. The filtrate was passed through silica gel bead. The filtrate was evaporated to dryness to give the product (0.21 g, 85.4%), as creamy paste, which was used as such in next step. 1H-NMR (CDCl3) 3.11 (s, 1H); 7.25-7.31 (m, 3H); 7.44-7.55 (m, 4H); 7.73 (d, 1H, J=7.69 Hz).

후처리

  1. customThe solvent was evaporated to dryness
  2. additionthe residue was diluted to 50 ml with EtOAc
  3. washwashed with H2O
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness

출처 및 근거

ORD 기록
ord-bd7229f3ebbe4683b508cd737f42bc88
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181182B2

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