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Diisopropylethylamine → Carbonic acid methyl ester 4-(2-trimethylsilanyl-ethoxymethoxy)-naphthalen-2-yl ester

HRID 1727011
Notes
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Reaction equation

HRID 1727011 reaction equation
[CH3:1][O:2][C:3](=[O:16])[O:4][C:5]1[CH:14]=[C:13]([OH:15])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1.[CH3:17][Si:18]([CH3:25])([CH3:24])[CH2:19][CH2:20][O:21][CH2:22]Cl.C(N(C(C)C)C(C)C)C>C(Cl)Cl>[CH3:17][Si:18]([CH3:25])([CH3:24])[CH2:19][CH2:20][O:21][CH2:22][O:15][C:13]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[C:5]([O:4][C:3](=[O:16])[O:2][CH3:1])[CH:14]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 15640638Carbonic acid 4-hydroxy-naphthalen-2-yl ester methyl ester

Product 1

HCID 69036509Carbonic acid methyl ester 4-(2-trimethylsilanyl-ethoxymethoxy)-naphthalen-2-yl esterYield 75.4%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Conditions

Temperature
2 °C

Procedure

4.62 g (21.2 mmol) of carbonic acid 4-hydroxy-naphthalen-2-yl ester methyl ester [Journal of Agricultural and Food Chemistry (1994), 42(12), 2970-2] was dissolved in 150 ml of MeCl2, 4.95 ml=4.71 g (25.4 mmol) of 2-(trimethylsilyl)-ethoxymethylchloride was added and this mixture cooled down to 2° C. 11.1 ml=8.38 g (63.5 mmol) of N-ethyl-diisoproylamine was added drop by drop and then, reaction was warmed up to ambient temperature. After 48 hours, it was poured into crashed ice and extracted twice with MeCl2; the organic phases were washed with water, dried (MgSO4) and evaporated. The crude product was purified by flash chromatography (SiO2, gradient of n-heptane/MeCl2) to give 5.57 g of carbonic acid methyl ester 4-(2-trimethylsilanyl-ethoxymethoxy)-naphthalen-2-yl ester as colorless oil.

Workup

  1. customreaction
  2. temperaturewas warmed up to ambient temperature
  3. additionit was poured
  4. extractionextracted twice with MeCl2
  5. washthe organic phases were washed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe crude product was purified by flash chromatography (SiO2, gradient of n-heptane/MeCl2)

Sources & evidence

ORD record
ord-7f2463cb43b14d6b96528473969ee07e
Source dataset
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07495001B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes