Tetrahydrofuran → HCID 59263148, 화합물

HRID 424103

반응식

HRID 424103 반응식
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8](Br)[C:7]([O:11][CH3:12])=[CH:6][C:5]=1[O:13][CH3:14].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:22]1[CH2:26]OC[CH2:23]1>O.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([C:22]([CH3:26])=[CH2:23])[C:7]([O:11][CH3:12])=[CH:6][C:5]=1[O:13][CH3:14]

참가 물질

7

반응물 3

HCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 3859236Methyl 5-bromo-2,4-dimethoxybenzoate

생성물 1

HCID 59263148HCID 59263148, 화합물

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

To potassium isopropylidene trifluoroborate (4.87 g, 32.7 mmol) and 5-bromo-2,4-dimethoxybenzoic acid methyl ester (7.5 g, 27.3 mmol) in THF (195 ml) was added Cs2CO3 (26.6 g, 81.8 mmol) in water (39 ml). The reaction was degassed and Pd(PPh3)4 (1.58 g, 1.36 mmol) added. The reaction was heated at reflux for three days then quenched by adding water and extracted with EtOAc (×2). The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated to leave an orange solid. The product was taken up in EtOAc again and the precipitate filtered. The filtrate was evaporated to dryness to yield 5-isopropenyl-2,4-dimethoxy-benzoic acid methyl ester (6.2 g). 1H NMR (Me-d3-OD) 7.68 (1H, s), 6.66 (1H, s), 5.10-5.08 (1H, m), 5.02-5.00 (1H, m), 3.93 (3H, s), 3.92 (3H, s), 3.84 (3H, s), 2.08-2.06 (3H, m). MS: [M+H]+ 237.

후처리

  1. customThe reaction was degassed
  2. temperatureThe reaction was heated
  3. temperatureat reflux for three days
  4. customthen quenched
  5. additionby adding water
  6. extractionextracted with EtOAc (×2)
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customevaporated
  11. customto leave an orange solid
  12. filtrationthe precipitate filtered
  13. customThe filtrate was evaporated to dryness

출처 및 근거

ORD 기록
ord-08a9916e00dd4ab2bdb830d9bb8bc2c7
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101648B2

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