Triethylamine → HCID 86587276、化合物

HRID 392813

反応式

HRID 392813 の反応式
[CH3:1][C:2]1([CH3:12])[O:6][C@@H:5]([CH2:7][C:8]([OH:10])=[O:9])[C:4](=[O:11])[O:3]1.C(O)(=O)[C@H](CC(O)=O)O.C(N(CC)CC)C.[C:29]([Si:33](Cl)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([CH3:32])([CH3:31])[CH3:30]>ClCCl.C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:12])[O:6][C@@H:5]([CH2:7][C:8]([O:10][Si:33]([C:29]([CH3:32])([CH3:31])[CH3:30])([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:9])[C:4](=[O:11])[O:3]1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 94078tert-ButyldiphenylchlorosilaneHCID 222656L-Malic AcidHCID 641720(S)-2-(2,2-Dimethyl-5-oxo-1,3-dioxolan-4-yl)acetic acid

生成物 1

HCID 86587276HCID 86587276、化合物収率 99.8%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of (S)-(+)-2,2-dimethyl-5-oxo-1,3-dioxolane-4-acetic acid (2.08 g, 11.9 mmol), which was derived from L-malic acid by means known in the art, in dry dichloromethane (20 ml) was treated with triethylamine (1.83 ml, 13.1 mmol) followed by a solution of t-butylchlorodiphenylsilane (3.44 g, 12.5 mmol) in dichloromethane (5 ml) added dropwise over 5 minutes. After 3 hours at 22° C., the reaction mixture was diluted with toluene (250 ml) washed with water, saturated sodium bicarbonate, brine and dried over magnesium sulfate. Evaporation of the solvent under reduced pressure and chromatography of the residue on silica gel (4×12 cm) using a mixture of toluene and ethyl acetate (0-2%) as eluent gave 4.90 g (99%) of the title material as a clear oil. 1H NMR (400 MHz, CDCl3) δ: 1.13 (s, 9), 1.58 (s, 3), 3.05 (m, 2), 4.79 (dd, 1, J=4, 7), 7.4-7.8 (m, 10).

後処理

  1. additionadded dropwise over 5 minutes
  2. washwashed with water, saturated sodium bicarbonate, brine
  3. dry with materialdried over magnesium sulfate
  4. customEvaporation of the solvent under reduced pressure and chromatography of the residue on silica gel (4×12 cm)
  5. additiona mixture of toluene and ethyl acetate (0-2%) as eluent

出典と根拠

ORDレコード
ord-cbfcffe2f321494b9f6b949aed7e6a8e
出典データセット
uspto-grants-2004_10
特許番号
US06803378B2

関連ノート

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