Toluene → HCID 68995354, 화합물

HRID 1182492노트

반응식

HRID 1182492 반응식
[S:1]1[CH:5]=[CH:4][C:3](B(O)O)=[CH:2]1.Br[C:10]1[CH:28]=[CH:27][C:13]([C:14]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:15])=[CH:12][CH:11]=1.C1(C)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>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.C(O)C>[CH2:25]([O:24][C:22](=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][C:14](=[O:15])[C:13]1[CH:12]=[CH:11][C:10]([C:3]2[CH:4]=[CH:5][S:1][CH:2]=2)=[CH:28][CH:27]=1)[CH3:26]

참가 물질

7

반응물 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 581760Thiophene-3-boronic acidHCID 11024292ETHYL 8-(4-BROMOPHENYL)-8-OXOOCTANOATE

생성물 1

HCID 68995354HCID 68995354, 화합물수율 20.3%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매

실험 절차

To a mixture of 3-thiophene boronic acid (383 mg, 3 mmol) and bromoester 49d (1.03 g, 3 mmol) were added anhydrous toluene (30 mL) and ethanol (1.5 mL) (20:1, c=1.0M) followed by 2M K2CO3 aqueous solution (3 mL, 6 mmol). The reaction mixture was stirred under nitrogen for 30 minutes and then Pd(PPh3)4 (191 mg, 5 mol %, 0.16 mmol) was quickly added. After 24 hours of reflux, the mixture was cooled to room temperature, filtered through a pad of Celite and rinsed with ethyl acetate (50 mL). The organic solution was washed with brine (30 mL), dried (MgSO4), and concentrated. Purification by flash silica gel chromatography (10% methanol in dichloromethane) followed by crystallization from ethyl acetate afforded the corresponding ester 115 (210 mg, 20% yield) as a white solid.

후처리

  1. temperatureAfter 24 hours of reflux
  2. filtrationfiltered through a pad of Celite
  3. washrinsed with ethyl acetate (50 mL)
  4. washThe organic solution was washed with brine (30 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customPurification by flash silica gel chromatography (10% methanol in dichloromethane)
  8. customfollowed by crystallization from ethyl acetate

출처 및 근거

ORD 기록
ord-55a085e35a524582a56a440cf84f3c45
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07288567B2

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