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Hydrochloric Acid → 4-Carboxybenzyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl sulfoxide

HRID 6517
ノート
印刷プレビュー

反応式

HRID 6517 の反応式
I([O-])(=O)(=O)=[O:2].[Na+].[CH3:7][C:8]1([CH3:31])[CH2:17][CH2:16][C:15]([CH3:19])([CH3:18])[C:14]2[CH:13]=[C:12]([S:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([OH:30])=[O:29])=[CH:24][CH:23]=3)[CH:11]=[CH:10][C:9]1=2.Cl>O.C(O)C.CN(C)C=O>[CH3:7][C:8]1([CH3:31])[CH2:17][CH2:16][C:15]([CH3:18])([CH3:19])[C:14]2[CH:13]=[C:12]([S:20]([CH2:21][C:22]3[CH:23]=[CH:24][C:25]([C:28]([OH:30])=[O:29])=[CH:26][CH:27]=3)=[O:2])[CH:11]=[CH:10][C:9]1=2
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 148505884-Carboxybenzyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl thioetherHCID 23667635Sodium periodate

生成物 1

HCID 148505894-Carboxybenzyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl sulfoxide収率 39.6%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒
HCID 962
Water
溶媒
2 回
HCID 6228Dimethylformamide溶媒

実験手順

A solution of 3.4 g (16 mmol) of sodium periodate in 30 ml of water was added dropwise to 5.3 g (15 mmol) of the thioether from Example 10 in a mixture of 150 ml of ethanol and 40 ml of dimethylformamide at 0° C., and the mixture was then stirred at the same temperature for 2 hours and at room temperature overnight. The reaction solution was then poured into water, the pH was adjusted to 5 with 2N hydrochloric acid, the mixture was extracted with dichloromethane, and the organic extracts were washed with water, dried over magnesium sulfate and evaporated under reduced pressure. Crystallization of the oily residue from ethanol yielded 2.2 g of title compound of melting point 198°-200° C.

後処理

  1. extractionthe mixture was extracted with dichloromethane
  2. washthe organic extracts were washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customCrystallization of the oily residue from ethanol

出典と根拠

ORDレコード
ord-3975e3cba1d24b4fba5c7e42d9b53709
出典データセット
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05248823

反応ノート

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