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Triphenylmethane → HCID 21999136, 화합물

HRID 1375130
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HRID 1375130 반응식
C([Li])CCC.[CH2:6]1[CH2:25][O:24][C:8]2([CH2:13][CH2:12][CH2:11][CH:10]([S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH:9]2[CH3:23])[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:9]2([CH3:23])[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:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH2:11][CH2:12][CH2:13][CH:8]2[O:24]1
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참가 물질

8

반응물 5

HCID 10614TriphenylmethaneHCID 25517Ammonium ChlorideHCID 1045071-Decanol, 10-bromo-HCID 21999137HCID 21999137, 화합물HCID 178418339Butyllithium

생성물 1

HCID 21999136HCID 21999136, 화합물수율 92%

시약·촉매·용매 2

HCID 8028
Tetrahydrofuran
용매
2회
HCID 12679Hexamethylphosphoramide용매

실험 절차

A solution of n-butyl lithium (1.02 ml) was added dropwise to a solution of 304 mg of 1,1-(ethylenedioxy)-2-methyl-3-(phenylsulfonyl)-cyclohexane and 4 mg of triphenylmethane in 5 ml of THF at −78° C. under an argon stream. After stirring for 10 minutes, the reaction was effected at room temperature for 1 hour. HMPA (1 ml) was added to the reaction mixture. It was then recooled to −78° C., followed by the dropwise addition of a solution of 90 mg of 10-bromo-1-decanol in 2 ml of THF. After 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 dried over magnesium sulfate. The solvent was then distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column while using hexane-ethyl acetate, whereby 1,2-(ethylenedioxy)-3-(10-hydroxydecyl)-2-methyl-3-(phenylsulfonyl)-cyclohexane was obtained in the form of a colorless oil. Yield: 92%, TLC: (hexane-AcOEt: 6-4) Rf=0.2

후처리

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

출처 및 근거

ORD 기록
ord-d8474d9abd9745f6bfdc2a7cb4856435
출처 데이터셋
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07166642B1

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