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

HRID 235692

반응식

HRID 235692 반응식
[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

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 4148881Lithium borohydride2회HCID 20219600Dimethyl[(2-methyl-1,3-dithiolan-2-yl)methyl]propanedioate

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-13ab7eda701f492ab48381689b0df212
출처 데이터셋
uspto-grants-1987_02
특허 번호
US04640913

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