3,4-Dihydroxybenzaldehyde → HCID 86608585, 화합물

HRID 1367796노트

반응식

HRID 1367796 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1O)[CH:5]=[O:6].[C:11](=[O:14])([O-])[O-].[Cs+].[Cs+].S(O[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])(=O)(=O)C>COCCOCCOC>[CH2:22]([O:1][C:2]1[C:3]([O:14][CH2:11][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]/[CH:29]=[CH:30]\[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]

참가 물질

5

반응물 3

HCID 87683,4-DihydroxybenzaldehydeHCID 10796Cesium carbonateHCID 6016198Oleyl methane sulfonate

생성물 1

HCID 86608585HCID 86608585, 화합물수율 89.2%

시약·촉매·용매 1

HCID 8150Diglyme용매

반응 조건

온도
100 °C

실험 절차

3,4-Dihydroxybenzaldehyde (2.76 g, 20.0 mmol) was weighed into a 200 mL round bottomed flask with a stir bar. The flask was charged with diglyme (100 mL), septum sealed and flushed with argon. Cesium carbonate (19.5 g, 60.0 mmol) was added to the solution slowly in portions. Oleyl mesylate (15.2 g, 44.0 mmol) was added via syringe. The reaction mixture was heated to 100° C. under slight positive pressure of argon. The reaction mixture was cooled to room temperature and filtered. The solids were washed with 1,2-dichloroethane. The combined filtrate and washes were concentrated and then dried under high vacuum at 65° C. to remove residual diglyme. The resultant yellow oil was purified via flash chromatography (5% ethyl acetate in hexanes) to afford 11.4 g (89%) of a yellow oil that turned to yellow wax upon standing at room temperature.

후처리

  1. customsealed
  2. customflushed with argon
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationfiltered
  5. washThe solids were washed with 1,2-dichloroethane
  6. concentrationThe combined filtrate and washes were concentrated
  7. customdried under high vacuum at 65° C.
  8. customto remove residual diglyme
  9. customThe resultant yellow oil was purified via flash chromatography (5% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-0852602064c342128361d32625709329
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893302B2

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