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

HRID 618491

Reaction equation

HRID 618491 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c07b12844fa04999ae1d2e3dafdb5ac0
Source dataset
uspto-grants-1999_09
Patent number
US05952382

Linked notes

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