2-(Dimethylamino)ethanol → 6-Hydroxy-2,5,7,8-tetramethyl-chroman-2-carboxylic acid 2-dimethylaminoethyl ester

HRID 16651

반응식

HRID 16651 반응식
[OH:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:17])([C:14]([OH:16])=[O:15])[CH2:6][CH2:5]2.C1(N=C=NC2CCCCC2)CCCCC1.[CH3:34][N:35]([CH2:37][CH2:38]O)[CH3:36].CCOC(C)=O>C(Cl)Cl.CCCCCC>[CH3:34][N:35]([CH3:36])[CH2:37][CH2:38][O:15][C:14]([C:7]1([CH3:17])[CH2:6][CH2:5][C:4]2[C:9](=[C:10]([CH3:13])[C:11]([CH3:12])=[C:2]([OH:1])[C:3]=2[CH3:18])[O:8]1)=[O:16]

참가 물질

7

반응물 4

HCID 79022-(Dimethylamino)ethanolHCID 8857Ethyl AcetateHCID 10868DicyclohexylcarbodiimideHCID 40634Trolox

생성물 1

HCID 113478116-Hydroxy-2,5,7,8-tetramethyl-chroman-2-carboxylic acid 2-dimethylaminoethyl ester수율 37.3%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8058Hexane용매

실험 절차

To a stirred solution of 6-hydroxy-2,5,7,8-tetramethyl-chroman-2-carboxylic acid (2.6 g, 10 mmol) in 80 mL of CH2Cl2 was added dicyclohexylcarbodiimide (2.2 g, 10 mmol). After stirring for 5 min, dimethylaminoethanol (0.93 g, 10 mmol) dissolved in 10 mL of CH2Cl2 was added to the mixture to form a cloudy suspension. The solution was stirred at room temperature overnight, and the resulting white suspension was filtered to give a clear solution. The solution was washed three times with water, and the organic layer was collected and dried over anhydrous sodium sulfate. The drying agent was removed by filtration and the filtrate was concentrated by rotary evaporation, yielding a viscous, yellowish oil. The residue obtained was loaded to a silica gel column with a mixed solvent of EtOAc and hexane (1:1, v/v). The column was eluted with EtOAc/hexane (1:1, v/v) to remove the less polar impurity. Subsequently, a mixed solvent of CH2Cl2/MeOH/NH4OH (90:10:0.5, v/v/v) was used to elute the desired product from the column. 1.2 g of 6-Hydroxy-2,5,7,8-tetramethyl-chroman-2-carboxylic acid 2-dimethylaminoethyl ester were obtained as a viscous yellowish oil, which solidified upon standing at room temperature. MS: m/z=322.2 (M+H+). 1H NMR (CDCl3, 300 Hz) 4.19 (t, J=5.8 Hz, 2H), 2.52-1.80 (m, 4H), 2.48 (t, 2H), 2.20 (s, 6H), 2.18 (s, 3H), 2.16 (s, 3H), 2.06 (s, 3H), 1.61 (s, 3H). 13C NMR (CDCl3, 75 Hz) 173.9, 145.6, 145.4, 122.5, 121.6, 118.8, 116.9, 77.0, 63.3, 57.5, 45.7, 30.6, 25.4, 21.0, 12.3, 11.9, 11.3.

후처리

  1. additionwas added to the mixture
  2. customto form a cloudy suspension
  3. stirringThe solution was stirred at room temperature overnight
  4. filtrationthe resulting white suspension was filtered
  5. customto give a clear solution
  6. washThe solution was washed three times with water
  7. customthe organic layer was collected
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe drying agent was removed by filtration
  10. concentrationthe filtrate was concentrated by rotary evaporation
  11. customyielding a viscous, yellowish oil
  12. customThe residue obtained
  13. washThe column was eluted with EtOAc/hexane (1:1
  14. customv/v) to remove the less polar impurity
  15. washto elute the desired product from the column

출처 및 근거

ORD 기록
ord-3fa06972e94f4ff5abee077af197335f
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737179B2

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