Hydrochloric Acid → 2-[(2-Methyl-1,3-dithiolan-2-yl)methyl]-1,3-propanediol

HRID 235692

反応式

HRID 235692 の反応式
[BH4-].[Li+].C[O:4][C:5](=O)[CH:6]([CH2:11][C:12]1([CH3:17])[S:16][CH2:15][CH2:14][S:13]1)[C:7](OC)=[O:8].Cl.[Cl-].[Na+]>O1CCCC1>[CH3:17][C:12]1([CH2:11][CH:6]([CH2:5][OH:4])[CH2:7][OH:8])[S:13][CH2:14][CH2:15][S:16]1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 4148881Lithium borohydride2 回HCID 20219600Dimethyl[(2-methyl-1,3-dithiolan-2-yl)methyl]propanedioate

生成物 1

HCID 202185072-[(2-Methyl-1,3-dithiolan-2-yl)methyl]-1,3-propanediol収率 85.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of about 14.53 g of lithium borohydride in about 630 ml of tetrahydrofuran at about 0° C. was added about 84.0 g of dimethyl[(2-methyl-1,3-dithiolan-2-yl)methyl]propanedioate dropwise. After the exotherm ended the mixture was stirred at room temperature for about 18 hours, then about 4.15 g of lithium borohydride were added and stirring was continued for about 20 hours. The solution was cooled in an ice bath, about 400 ml of about 6N hydrochloric acid were added dropwise, the mixture was saturated with sodium chloride and then extracted with ether. The ether layer was washed with brine, then saturated sodium bicarbonate, dried and the solvent removed. Methanol was added and removed three times. The solid was recrystallized from carbon tetrachloride, giving about 56.77 g of the desired title compound, mp 72°-73° C.

後処理

  1. stirringstirring
  2. waitwas continued for about 20 hours
  3. temperatureThe solution was cooled in an ice bath
  4. extractionextracted with ether
  5. washThe ether layer was washed with brine
  6. dry with materialsaturated sodium bicarbonate, dried
  7. customthe solvent removed
  8. additionMethanol was added
  9. customremoved three times
  10. customThe solid was recrystallized from carbon tetrachloride

出典と根拠

ORDレコード
ord-13ab7eda701f492ab48381689b0df212
出典データセット
uspto-grants-1987_02
特許番号
US04640913

関連ノート

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