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Tetrahydrofuran → 2-Decyl-6-methoxynaphthalene

HRID 1476362
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HRID 1476362 반응식
C1COCC1.[CH2:6]([Mg]Br)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].C(Br)CCCCCCCCC.Br[C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][CH:39]=1)[CH:36]=[C:35]([O:40][CH3:41])[CH:34]=[CH:33]2>O.Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:6]([C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][CH:39]=1)[CH:36]=[C:35]([O:40][CH3:41])[CH:34]=[CH:33]2)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8028Tetrahydrofuran3회HCID 81731-BromodecaneHCID 787862-Bromo-6-methoxynaphthaleneHCID 178418384HCID 178418384, 화합물

생성물 1

HCID 867043812-Decyl-6-methoxynaphthalene

시약·촉매·용매 2

HCID 178418745HCID 178418745, 화합물촉매
HCID 962
Water
용매

실험 절차

A THF solution of n-decyl magnesium bromide (prepared as a THF (2 ml) solution of n-decyl bromide (2.2 ml, 11 mmol) and Mg (292 mg, 12 mmol)) was added to 6-bromo-2-methoxynaphthalene (2.37 g, 10 mmol) easily available from a reagent manufacturer and a THF (10 ml) solution of Ni(dppp)Cl2 (271 mg, 0.5 mmol), and the mixture was heated under reflux for 19 hours. After cooling, the mixed solution was diluted with water (10 ml), and non-reacted Mg was filtered out. The filtered solution was extracted with ether (5 ml×3). The extracted organic phases were collected (10 ml×3), and dried with MgSO4, and condensed with an evaporator. The condensed organic phase was recrystallized with hexane to obtain 6-n-decyl-2-methoxynaphthalene (compound (3)-64) as a light yellow solid.

후처리

  1. temperatureunder reflux for 19 hours
  2. temperatureAfter cooling
  3. filtrationwas filtered out
  4. extractionThe filtered solution was extracted with ether (5 ml×3)
  5. customThe extracted organic phases were collected (10 ml×3)
  6. dry with materialdried with MgSO4, and condensed with an evaporator
  7. customThe condensed organic phase was recrystallized with hexane

출처 및 근거

ORD 기록
ord-0a539def97724f5f858adcdbbc2c0a6c
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09018630B2

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