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

HRID 432154

반응식

HRID 432154 반응식
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[S:12](Cl)([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13].O>N1C=CC=CC=1>[CH3:19][C:18]1[CH:20]=[CH:21][C:15]([S:12]([O:11][CH:8]2[CH2:9][CH2:10][C:5]3([O:4][CH2:3][CH2:2][O:1]3)[CH2:6][CH2:7]2)(=[O:14])=[O:13])=[CH:16][CH:17]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 5673521,4-Dioxaspiro(4.5)decan-8-ol2회

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a stirred solution of 1,4-dioxaspiro[4.5]decan-8-ol (Intermediate M) (99.8 g, 0.63 mol) in pyridine (450 mLs) at 0° C. under nitrogen was added tosylchloride (132.4 g, 0.69 mol) portionwise such that T<2° C. On complete addition, the mixture was allowed to warm slowly to room temperature and stirred at room temperature overnight. Treated with water (750 mL) and extracted with EtOAc (500 mL then 2×250 mL). Combined extracts were washed with 3N HCl (3×300 mL), brine (300 mL) and dried over Na2SO4. Filtered and evaporated to yield a pale yellow oil (200 g crude). This oil was treated with petroleum ether (40-60°) (200 mL) and scratched to induce solid formation. 1,4-dioxaspiro[4.5]dec-8-yl 4-methyl-1-benzenesulfonate was filtered, washed with petroleum ether (40-60°) (200 mL) and dried in vacuo. Yield=181.0 g, 92%.

후처리

  1. additionOn complete addition
  2. extractionextracted with EtOAc (500 mL
  3. washCombined extracts were washed with 3N HCl (3×300 mL), brine (300 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationFiltered
  6. customevaporated
  7. customto yield a pale yellow oil (200 g crude)
  8. filtration1,4-dioxaspiro[4.5]dec-8-yl 4-methyl-1-benzenesulfonate was filtered
  9. washwashed with petroleum ether (40-60°) (200 mL)
  10. customdried in vacuo

출처 및 근거

ORD 기록
ord-ad582436d4ff43d2bfd0242dfa745c29
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06660744B1

연결된 노트

불러오는 중…