Acetic Acid → 7,9,10-Trimethyl-2,4-dipropyl-7-(4,8,12-trimethyl-tridecyl)-4,5,6,7-tetrahydro-1,3,8-trioxa-phenanthrene

HRID 63809

反応式

HRID 63809 の反応式
[CH:1](=[O:5])[CH2:2][CH2:3][CH3:4].[CH3:6][C:7]1[C:16]([CH3:17])=[C:15]2[C:10]([CH2:11][CH2:12][C@:13]([CH2:19][CH2:20][CH2:21][C@@H:22]([CH2:24][CH2:25][CH2:26][C@@H:27]([CH2:29][CH2:30][CH2:31][CH:32]([CH3:34])[CH3:33])[CH3:28])[CH3:23])([CH3:18])[O:14]2)=[CH:9][C:8]=1[OH:35].CCO[C:39]([CH3:41])=O.[CH3:42][C:43](O)=O>OS(O)(=O)=O.O>[CH3:18][C:13]1([CH2:19][CH2:20][CH2:21][CH:22]([CH3:23])[CH2:24][CH2:25][CH2:26][CH:27]([CH3:28])[CH2:29][CH2:30][CH2:31][CH:32]([CH3:34])[CH3:33])[O:14][C:15]2[C:10](=[C:9]3[C:8](=[C:7]([CH3:6])[C:16]=2[CH3:17])[O:35][CH:42]([CH2:43][CH2:39][CH3:41])[O:5][CH:1]3[CH2:2][CH2:3][CH3:4])[CH2:11][CH2:12]1

参加物

7

反応物 4

HCID 176Acetic Acid2 回HCID 261ButanalHCID 8857Ethyl AcetateHCID 92729(+)-gamma-Tocopherol

生成物 1

HCID 684971007,9,10-Trimethyl-2,4-dipropyl-7-(4,8,12-trimethyl-tridecyl)-4,5,6,7-tetrahydro-1,3,8-trioxa-phenanthrene収率 100%

試薬・触媒・溶媒 2

HCID 1118Sulfuric Acid触媒HCID 962Water溶媒

実験手順

A 25 mL RBF was charged with butyraldehyde (155 mg, 2.16 mmol), AcOH (2 mL) and H2SO4 (1 drop). To the flask was then added a solution of (+)-γ-tocopherol (Ex-1C-1) (300 mg, 0.72 mmol) in AcOH (3 mL) dropwise over 2 h via syringe pump. The reaction was then stirred for 16 h and monitored by TLC (9:1 Hept:EtOAc). The reaction was then diluted with water (15 mL) and extracted with DCM (3×20 mL). The combined organic layers were washed with water (3×15 mL), dried over Na2SO4, filtered and concentrated by rotary evaporation to yield 7,9,10-trimethyl-2,4-dipropyl-7-(4,8,12-trimethyl-tridecyl)-4,5,6,7-tetrahydro-1,3,8-trioxa-phenanthrene (Ex-1C-2) as a brownish oil (425 mg, >100%), which was used without further purification.

後処理

  1. extractionextracted with DCM (3×20 mL)
  2. washThe combined organic layers were washed with water (3×15 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation

出典と根拠

ORDレコード
ord-128bc00887994050a25505632883fba9
出典データセット
uspto-grants-2016_09
特許番号
US09447006B2

関連ノート

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