Pyridine → 1,4-Dioxaspiro[4.5]decan-8-ol, 8-(4-methylbenzenesulfonate)

HRID 358353

반응식

HRID 358353 반응식
[OH:1][CH:2]1[CH2:11][CH2:10][C:5]2([O:9][CH2:8][CH2:7][O:6]2)[CH2:4][CH2:3]1.N1C=CC=CC=1.[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>O>[S:24]([O:1][CH:2]1[CH2:11][CH2:10][C:5]2([O:6][CH2:7][CH2:8][O:9]2)[CH2:4][CH2:3]1)([C:21]1[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=1)(=[O:26])=[O:25]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 5673521,4-Dioxaspiro(4.5)decan-8-ol

생성물 1

HCID 5674891,4-Dioxaspiro[4.5]decan-8-ol, 8-(4-methylbenzenesulfonate)

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
7 °C

실험 절차

A mixture of 8-hydroxy-1,4-dioxaspiro[4.5]decane (237 g, 1.5 mol) and 700 ml of pyridine was stirred at 0° C. while p-toluenesulfonyl chloride was added portion-wise. After the addition was completed the mixture was stirred for two days at 7° C. The mixture was poured into a 4-kg mixture of equal parts of ice and water with vigorous stirring. After about fifteen minutes a solid separated; this was filtered and washed with water. Dissolved the solid in CH2Cl2 and separated CH2Cl2 solution from residual water. The organic layer was dried (K2CO3 --Na2SO4), filtered and concentrated in vacuo at 36° C. The solution remaining was diluted with Skellysolve B and cooled to -75° C. with stirring. The white solid was filtered and dried in vacuo to give 435 g (92.9%), mp 65°-67.5° C. of the subtitled intermediate. IR C=C (1600), --SO2O-- (1350, 1180), C--O/S--O--C (1105, 945, 925), --SO3 -- (675); nmr (CDCl3) was in accordance with the structure assignment; mass spectrum m/e 312 (M+).

후처리

  1. additionwas added portion-wise
  2. additionAfter the addition
  3. customAfter about fifteen minutes a solid separated
  4. filtrationthis was filtered
  5. washwashed with water
  6. dissolutionDissolved the solid in CH2Cl2
  7. customseparated CH2Cl2 solution from residual water
  8. dry with materialThe organic layer was dried (K2CO3 --Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo at 36° C
  11. additionThe solution remaining was diluted with Skellysolve B
  12. temperaturecooled to -75° C.
  13. stirringwith stirring
  14. filtrationThe white solid was filtered
  15. customdried in vacuo

출처 및 근거

ORD 기록
ord-daad77754f0c44b2ba790bd501703bcd
출처 데이터셋
uspto-grants-1984_08
특허 번호
US04466977

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