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Thioglycolic Acid → (2S)-2-[((S)-6-Methoxy-alpha-methyl-2-naphthalenacetyloxy)methyl]-1,3-oxathiolan-5-one

HRID 844517
ノート
印刷プレビュー

反応式

HRID 844517 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C@H:13]([CH3:23])[C:14]([O:16][CH2:17][CH:18](OC)OC)=[O:15])[CH:7]=[CH:6]2.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.S([O-])([O-])(=O)=O.[Mg+2].[SH:45][CH2:46][C:47]([OH:49])=[O:48]>ClC(Cl)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C@H:13]([CH3:23])[C:14]([O:16][CH2:17][C@@H:18]1[S:45][CH2:46][C:47](=[O:49])[O:48]1)=[O:15])[CH:7]=[CH:6]2
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 1133Thioglycolic AcidHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 24083Sulfuric acid magnesium salt (1:1)HCID 867580112,2-dimethoxyethyl (S)-6-methoxy-alpha-methyl-2-naphthaleneacetate

生成物 1

HCID 70161980(2S)-2-[((S)-6-Methoxy-alpha-methyl-2-naphthalenacetyloxy)methyl]-1,3-oxathiolan-5-one収率 53.3%

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒2 回

実験手順

To a round bottom flask is added 2,2-dimethoxyethyl (S)-6-methoxy-α-methyl-2-naphthaleneacetate (13.8 g), dichloroethane (60 mL), camphorsulfonic acid (0.7 g) and magnesium sulfate (1.0 g). The reaction mixture is heated to reflux and a solution of mercaptoacetic acid (13.5 g) in dichloroethane (15 mL) is added dropwise. The mixture is removed from the oil bath and a sample is taken for TLC and NMR analysis. Additional camphorsulfonic acid (0.6 g) is added and the mixture is heated in an oil bath to reflux for 2 hours. The mixture is cooled to room temperature and then shaken with water (50 mL) and saturated sodium bicarbonate (50 mL). The separated lower phase is shaken with saturated sodium bicarbonate (25 mL) and water (50 mL), the phases are separated and the lower cloudy organic phase is vacuum concentrated to give 17.4 g of crude product. The obtained syrup is applied to a silica column and eluted with EtOAc/heptanes (15:85) to provide 8.0 g of product.

後処理

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux
  3. customThe mixture is removed from the oil bath
  4. additionAdditional camphorsulfonic acid (0.6 g) is added
  5. temperaturethe mixture is heated in an oil bath
  6. temperatureto reflux for 2 hours
  7. customThe separated lower phase
  8. stirringis shaken with saturated sodium bicarbonate (25 mL) and water (50 mL)
  9. customthe phases are separated
  10. concentrationconcentrated
  11. customto give 17.4 g of crude product
  12. washeluted with EtOAc/heptanes (15:85)

出典と根拠

ORDレコード
ord-397ce8a51bc8457c8d4d5dcc8db588cf
出典データセット
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06380388B1

反応ノート

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