Hydrochloric Acid → Methyl 5-Hydroxy-2-tert-butyldimethylsilyloxymethyl-4-methoxyhydrocinnamate

HRID 1898763ノート

反応式

HRID 1898763 の反応式
C([O:4][C:5]1[C:6]([O:26][CH3:27])=[CH:7][C:8]([CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])=[C:9]([CH:16]=1)[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])(=O)C.C(=O)([O-])[O-].[K+].[K+].Cl>CO.O>[OH:4][C:5]1[C:6]([O:26][CH3:27])=[CH:7][C:8]([CH2:17][O:18][Si:19]([C:22]([CH3:23])([CH3:24])[CH3:25])([CH3:20])[CH3:21])=[C:9]([CH:16]=1)[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 23372362Methyl 5-acetoxy-2-tert-butyldimethylsilyloxymethyl-4-methoxyhydrocinnamate

生成物 1

HCID 23372374Methyl 5-Hydroxy-2-tert-butyldimethylsilyloxymethyl-4-methoxyhydrocinnamate

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

A mixture of methyl 5-acetoxy-2-tert-butyldimethylsilyloxymethyl-4-methoxyhydrocinnamate (4.64 g) and potassium carbonate (0.16 g) in anhydrous methanol (50 ml) is stirred at 0°-5° C. for about 18 hours, diluted with water, and the pH adjusted to 5 with dilute HCl. The mixture is extracted with ether and the ether solution is washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified by HPLC, eluting with 20% ethyl acetate in hexanes to give the desired product.

後処理

  1. extractionThe mixture is extracted with ether
  2. washthe ether solution is washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by HPLC
  7. washeluting with 20% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-2114d28bad454af9b4c8e60deb539fb3
出典データセット
uspto-grants-1996_11
特許番号
US05571506

反応ノート

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