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

HRID 257104

反応式

HRID 257104 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 28928tert-Butyldimethylsilyl chloride触媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7f6241b608384da19a8444e2067669df
出典データセット
uspto-grants-1993_11
特許番号
US05260310

関連ノート

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