Toluene → HCID 68995354、化合物

HRID 1182492ノート

反応式

HRID 1182492 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 68995354HCID 68995354、化合物収率 20.3%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-55a085e35a524582a56a440cf84f3c45
出典データセット
uspto-grants-2007_10
特許番号
US07288567B2

反応ノート

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