Sodium Carbonate → 4-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)benzoic acid

HRID 1443418노트

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HRID 1443418 반응식
[C:1]([C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][CH:5]=1)([OH:3])=[O:2].FC(F)(F)S(O[C:19]1[CH2:28][CH2:27][C:22]2([O:26][CH2:25][CH2:24][O:23]2)[CH2:21][CH:20]=1)(=O)=O.C([O-])([O-])=O.[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[O:23]1[C:22]2([CH2:27][CH2:28][C:19]([C:7]3[CH:8]=[CH:9][C:4]([C:1]([OH:3])=[O:2])=[CH:5][CH:6]=3)=[CH:20][CH2:21]2)[O:26][CH2:25][CH2:24]1

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 3121834-Carboxyphenylboronic AcidHCID 114830861,4-Dioxaspiro[4.5]dec-7-en-8-yl trifluoromethanesulfonate

생성물 1

HCID 595560954-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)benzoic acid수율 38.4%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

To a solution of 4-carboxyphenylboronic acid (0.69 g, 3.53 mmol) and 1,4-dioxaspiro[4.5]dec-7-en-8-yl trifluoromethanesulfonate (1.02 g, 3.53 mmol) in 14 mL of DMF were added 7 mL of 2 N aqueous solution of Na2CO3, triphenylphosphine (159 mg, 0.61 mmol), and tris(dibenzylideneacetone)dipalladium(0) (68 mg, 74.2 μmol). After stirring at 80° C. for 3 h and then at rt for 16 h, the mixture was concentrated and partitioned between 100 mL of Et2O and 150 mL of H2O. The aqueous layer was separated and acidified to pH ˜2-3 using concentrated HCl, and extracted with CH2Cl2 (2×100 mL). The organic layers were combined, dried over Na2SO4, and concentrated. The residue was re-crystallized from 10 mL of EtOAc to give 353 mg (38%) of the title compound.

후처리

  1. waitat rt for 16 h
  2. concentrationthe mixture was concentrated
  3. custompartitioned between 100 mL of Et2O and 150 mL of H2O
  4. customThe aqueous layer was separated
  5. extractionextracted with CH2Cl2 (2×100 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was re-crystallized from 10 mL of EtOAc

출처 및 근거

ORD 기록
ord-0e489130b3e44dfe81078b3cabfffdd1
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07659294B2

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