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

HRID 1383087노트

반응식

HRID 1383087 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-9ff4b8c3172e4fa6a37d7b03ecd59a5b
출처 데이터셋
uspto-grants-1989_02
특허 번호
US04808736

반응 노트

불러오는 중…