Triphenylmethane → 1,1-(Ethylenedioxy)-3-(10-hydroxydecyl)-4-methyl-3-(phenylsulfonyl)-cyclohexane

HRID 1375123노트

반응식

HRID 1375123 반응식
C([Li])CCC.[CH2:6]1[CH2:25][O:24][C:8]2([CH2:13][CH2:12][CH:11]([CH3:14])[CH:10]([S:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH2:9]2)[O:7]1.C1(C(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][OH:56].[Cl-].[NH4+]>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C>[CH2:25]1[CH2:6][O:7][C:8]2([CH2:13][CH2:12][CH:11]([CH3:14])[C:10]([CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][OH:56])([S:15]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)(=[O:17])=[O:16])[CH2:9]2)[O:24]1

참가 물질

8

반응물 5

HCID 10614TriphenylmethaneHCID 25517Ammonium ChlorideHCID 1045071-Decanol, 10-bromo-HCID 22394927HCID 22394927, 화합물HCID 178418339Butyllithium

생성물 1

HCID 219991391,1-(Ethylenedioxy)-3-(10-hydroxydecyl)-4-methyl-3-(phenylsulfonyl)-cyclohexane수율 97%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 12679Hexamethylphosphoramide용매

실험 절차

A solution of n-butyl lithium (1.8 ml) was added dropwise to a solution of 560 mg of 1,1-(ethylenedioxy)-4-methyl-3-(phenylsulfonyl)-cyclohexane and 4 mg of triphenylmethane in 5 ml of THF under argon stream at −78° C. The resulting mixture was stirred for 10 minutes and then reacted at room temperature for 1 hour. HMPA (1 ml) was added and the resulting mixture was recooled to −78° C., followed by the dropwise addition of a solution of 166 mg of 10-bromo-1-decanol in 2 ml of THF. After stirring the reaction at −20° C. for 2 hours, the reaction mixture was poured into a saturated solution of ammonium chloride. The resulting mixture was extracted with ethyl ether. The organic layer was washed with water and saturated saline and then, dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column while using hexane-ethyl acetate, whereby 1,1-(ethylenedioxy)-3-(10-hydroxydecyl)-4-methyl-3-(phenylsulfonyl)-cyclohexane was obtained in the form of a colorless oil. Yield: 97%, TLC: (hexane-AcOEt: 6-4) Rf=0.14

후처리

  1. customreacted at room temperature for 1 hour
  2. customwas recooled to −78° C.
  3. stirringAfter stirring
  4. customthe reaction at −20° C. for 2 hours
  5. extractionThe resulting mixture was extracted with ethyl ether
  6. washThe organic layer was washed with water and saturated saline
  7. dry with materialdried over magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customThe residue was purified by chromatography on a silica gel column

출처 및 근거

ORD 기록
ord-ef0cd7e384c240e698164ff4c2304b94
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07166642B1

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