3,4-Dihydroxybenzaldehyde → HCID 86608585、化合物

HRID 638770ノート

反応式

HRID 638770 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 86608585HCID 86608585、化合物収率 89.2%

試薬・触媒・溶媒 1

HCID 8150Diglyme溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ecb110a81951442c9389d15c9d461f64
出典データセット
uspto-grants-2010_04
特許番号
US07691405B2

反応ノート

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