Water → (S)-4-(2,5-dimethoxy-3,4,6-trimethylphenyl)-2-methyl-1,2-butanediol

HRID 1383087ノート

反応式

HRID 1383087 の反応式
[CH3:1][C@:2]([OH:7])([CH2:5]Cl)[CH2:3][OH:4].[CH3:8][O:9][C:10]1[C:15]([CH3:16])=[C:14]([CH3:17])[C:13]([O:18][CH3:19])=[C:12]([CH3:20])[C:11]=1[CH3:21].[H-].[Na+].O>O1CCOCC1>[CH3:1][C@:2]([OH:7])([CH2:5][CH2:17][C:14]1[C:15]([CH3:16])=[C:10]([O:9][CH3:8])[C:11]([CH3:21])=[C:12]([CH3:20])[C:13]=1[O:18][CH3:19])[CH2:3][OH:4]

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 6017651,4-Dimethoxy-2,3,5,6-tetramethylbenzeneHCID 11469077(2R)-2-methyl-3-chloropropane-1,2-diol

生成物 1

HCID 11129761(S)-4-(2,5-dimethoxy-3,4,6-trimethylphenyl)-2-methyl-1,2-butanediol収率 88.7%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

2.4 g (19.6 mmol) of (2R)-2-methyl-3-chloropropane-1,2-diol and 4.28 g (22 mmol) of 2,5-dimethoxy-1,3,4,6-tetramethylbenzene were dissolved in 20 ml of dioxane and heated to reflux temperature within 1 hour with 1.27 g (66 mmol) of sodium hydride (80% in mineral oil) and 0.1 ml of polyethylene glycol 400 (as the phase transfer catalyst) and stirred at this temperature for 16 hours. The mixture was then treated with 50 ml of water, filtered and washed with water. The residue was recrystallized from ether/hexane and there were obtained 4.91 g of (2S)-2-methyl-4-(2,5-dimethoxy-3,4,6-trimethylphenyl)-1,2-butanediol in the form of white crystals with a melting point of 82°-84° C. and [α]D20 =+2.86° (c=1.5% in CHCl3).

後処理

  1. temperatureheated
  2. filtrationfiltered
  3. washwashed with water
  4. customThe residue was recrystallized from ether/hexane

出典と根拠

ORDレコード
ord-9ff4b8c3172e4fa6a37d7b03ecd59a5b
出典データセット
uspto-grants-1989_02
特許番号
US04808736

反応ノート

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