Triethylamine → n-Butyl 3-(2-methoxyethoxymethoxy)-1-adamantanecarboxylate

HRID 1699154Notes

Reaction equation

HRID 1699154 reaction equation
[OH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][C:4]([C:12]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:13])([CH2:5]3)[CH2:3]1)[CH2:9]2.[CH3:19][O:20][CH2:21][CH2:22][O:23][CH2:24]Cl.C(N(CC)CC)C>C1COCC1>[CH3:19][O:20][CH2:21][CH2:22][O:23][CH2:24][O:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][C:4]([C:12]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:13])([CH2:5]3)[CH2:3]1)[CH2:9]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 12010642n-Butyl 3-hydroxy-1-adamantanecarboxylate2×

Product 1

HCID 18323397n-Butyl 3-(2-methoxyethoxymethoxy)-1-adamantanecarboxylateYield 94.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 200 mmol of n-butyl 3-hydroxy-1-adamantanecarboxylate, 220 mmol of 2-methoxyethoxymethyl chloride, 220 mmol of triethylamine and 200 ml of THF was refluxed for 3 hours. The reaction mixture was concentrated and subjected to column chromatography on a silica gel to give n-butyl 3-(2-methoxyethoxymethoxy)-1-adamantanecarboxylate (yield: 94.1%) at a conversion rate from n-butyl 3-hydroxy-1-adamantanecarboxylate of 99%.

Workup

  1. temperaturewas refluxed for 3 hours
  2. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-80ed0485035b48919483bea2819369e0
Source dataset
uspto-grants-2002_02
Patent number
US06344590B1

Reaction notes

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