Sodium hydride → 1-(7-Bromo-3-((2-methoxyethoxy)methoxy)naphthalen-2-yl)adamantane

HRID 618491

반응식

HRID 618491 반응식
[C:1]12([C:11]3[C:12]([OH:22])=[CH:13][C:14]4[C:19]([CH:20]=3)=[CH:18][C:17]([Br:21])=[CH:16][CH:15]=4)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[H-].[Na+].[CH3:25][O:26][CH2:27][CH2:28][O:29][CH2:30]Cl>CN(C=O)C>[C:1]12([C:11]3[CH:20]=[C:19]4[C:14]([CH:15]=[CH:16][C:17]([Br:21])=[CH:18]4)=[CH:13][C:12]=3[O:22][CH2:25][O:26][CH2:27][CH2:28][O:29][CH3:30])[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 145490723-(Adamantan-1-yl)-6-bromonaphthalen-2-ol

생성물 1

HCID 573012871-(7-Bromo-3-((2-methoxyethoxy)methoxy)naphthalen-2-yl)adamantane

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

17.85 g (0.05 mol) of 3-(1-adamantyl)-6-bromo-2-naphthol and 200 ml of DMF were introduced into a three-necked flask under a stream of nitrogen. 1.8 g (0.06 mol) of sodium hydride (80% in oil) was added portionwise and the reaction mixture was stirred until gas evolution had ceased. 6.9 ml (0.06 mol) of methoxyethoxymethyl chloride were then added and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into ice-cold water and extracted with ethyl ether and the organic phase was separated by settling, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a silica column eluted with a mixture of dichloromethane and heptane (40/60). 19.5 g (87%) of the expected compound were collected, which compound had a melting point of 99°-100° C.

후처리

  1. stirringthe reaction mixture was stirred at room temperature for 2 hours
  2. additionThe reaction mixture was poured into ice-cold water
  3. extractionextracted with ethyl ether
  4. customthe organic phase was separated
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue obtained
  8. customwas purified by chromatography on a silica column
  9. washeluted with a mixture of dichloromethane and heptane (40/60)
  10. custom19.5 g (87%) of the expected compound were collected

출처 및 근거

ORD 기록
ord-c07b12844fa04999ae1d2e3dafdb5ac0
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05952382

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