Triethylamine → (R)-3-[(1,1-dimethylethyl)dimethylsilyloxy]tetradecanoic acid

HRID 257104

반응식

HRID 257104 반응식
[OH:1][C@H:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:3][C:4]([O:6]C)=[O:5].[C:19]([Si:23]([CH3:26])([CH3:25])Cl)([CH3:22])([CH3:21])[CH3:20].C(N(CC)CC)C.Cl.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(Cl)Cl.C([Si](C)(C)Cl)(C)(C)C>[CH3:20][C:19]([Si:23]([CH3:26])([CH3:25])[O:1][C@H:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:3][C:4]([OH:6])=[O:5])([CH3:22])[CH3:21]

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 11130Triethylamine hydrochlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 98349453R-hydroxymyristic acid methyl ester

생성물 1

HCID 54310188(R)-3-[(1,1-dimethylethyl)dimethylsilyloxy]tetradecanoic acid수율 103.5%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 28928tert-Butyldimethylsilyl chloride촉매HCID 6344Dichloromethane용매

실험 절차

50 g of methyl (R)-3-hydroxytetradecanoate, 35 g of t-butyldimethylchlorosilane, 6.1 g of 4-dimethylaminopyridine and 29.4 g of triethylamine were dissolved in 200 ml of methylene chloride and stirred at room temperature for 30 hours as well as under reflux for 16 hours. Thereupon, a further 2 g of t-butyldimethylchlorosilane were added. After a further 24 hours under reflux the precipitated triethylamine hydrochloride salt was filtered off, washed with ether and the filtrate was concentrated. The residue was dissolved in ether and washed in sequence with water, 0.5M citric acid, again with water and saturated sodium chloride solution, dried, concentrated and subsequently freed from volatile material at 5° C. in a high vacuum for 5 hours. There were obtained 71.8 g of (R)-3-[(1,1-dimethylethyl)dimethylsilyloxy]tetradecanoic acid, IR (cm-1): 1745, 1254, 895, 776.

후처리

  1. temperatureunder reflux for 16 hours
  2. filtrationwas filtered off
  3. washwashed with ether
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe residue was dissolved in ether
  6. washwashed in sequence with water, 0.5M citric acid, again with water and saturated sodium chloride solution
  7. customdried
  8. concentrationconcentrated
  9. waitsubsequently freed from volatile material at 5° C. in a high vacuum for 5 hours

출처 및 근거

ORD 기록
ord-7f6241b608384da19a8444e2067669df
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05260310

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