2,6-Lutidine → Methyl 4-(adamantan-1-ylmethoxy)-5-(1-((tert-butyldimethylsilyl)oxy)-ethyl)-2-fluorobenzoate

HRID 1849735Notes

Reaction equation

HRID 1849735 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[C:8]([CH:10]([OH:12])[CH3:11])[C:7]([O:13][CH2:14][C:15]23[CH2:24][CH:19]4[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]4)[CH2:16]2)[CH2:22]3)=[CH:6][C:5]=1[F:25].N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si:41]([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:43])[CH3:42])(=O)=O>ClCCl>[C:15]12([CH2:14][O:13][C:7]3[C:8]([CH:10]([O:12][Si:41]([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:43])[CH3:42])[CH3:11])=[CH:9][C:4]([C:3]([O:2][CH3:1])=[O:26])=[C:5]([F:25])[CH:6]=3)[CH2:24][CH:19]3[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]3)[CH2:16]1)[CH2:22]2

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 86703607Methyl 4-(adamantan-1-ylmethoxy)-2-fluoro-5-(1-hydroxyethyl)benzoate

Product 1

HCID 86703613Methyl 4-(adamantan-1-ylmethoxy)-5-(1-((tert-butyldimethylsilyl)oxy)-ethyl)-2-fluorobenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl-4-(adamantan-1-ylmethoxy)-2-fluoro-5-(1-hydroxyethyl)benzoate (0.26 g, 0.72 mmol) and 2,6-lutidine (0.17 mL, 1.44 mmol) in anhydrous dichloromethane (5 mL) was added tert-butyldimethylsilyl trifluoromethanesulfonate (0.285 g, 1.08 mmol) at 0° C. The reaction mixture was allowed to warm to ambient temperature and stirred for 1 hour. After dilution with dichloromethane (100 mL), the organic phase was washed with 1 N hydrochloric acid (2×5 mL), brine (10 mL), and dried over anhydrous sodium sulfate. Filtration and concentration of the filtrate in vacuo afforded methyl 4-(adamantan-1-ylmethoxy)-5-(1-((tert-butyldimethylsilyl)- oxy)ethyl)-2-fluorobenzoate as a yellowish oil (0.35 g, quant.), which was used without further purification.

Workup

  1. washAfter dilution with dichloromethane (100 mL), the organic phase was washed with 1 N hydrochloric acid (2×5 mL), brine (10 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationFiltration and concentration of the filtrate in vacuo

Sources & evidence

ORD record
ord-beb82c7ff54f42c294a3a61e647b1613
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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