Sodium hydride → (2-Iodo-3-methyl-benzyloxy)-acetic acid tert-butyl ester

HRID 2216044Notes

Reaction equation

[I:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][OH:10].[H-].[Na+].[C:13]([O:17][C:18](=[O:21])[CH2:19]Br)([CH3:16])([CH3:15])[CH3:14]>CN(C=O)C>[C:13]([O:17][C:18](=[O:21])[CH2:19][O:10][CH2:9][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([CH3:8])[C:2]=1[I:1])([CH3:16])([CH3:15])[CH3:14]

Participants

Conditions

Temperature: 0 °C

Procedure

(2-Iodo-3-methyl-phenyl)-methanol (1608 mg, 6.8 mmol, Example 131: step b) was dissolved into DMF (10 mL). The solution was cooled to 0° C. To this was added sodium hydride in one portion and the reaction continued to stir at 0° C. for 30 minutes. To the cooled solution was added t-butylbromoacetate (1.3 mL, 8.9 mmol) and then the reaction was warmed to RT and then heated to 50° C. for 4 hours. The solvents were removed in vacuo and the resulting residue was dissolved into EtOAc and washed with brine. The combined organic layers were dried (MgSO4) and the solvent was removed in vacuo resulting in the title compound (1.29 g, 53%) that was used with out further purification. 1H-NMR (CDCl3): δ 7.28–7.13 (m, 3H), 4.63 (s, 2H), 4.07 (s, 2H), 2.44 (s, 3H), 1.47 (s, 9H).

Workup

temperaturethe reaction was warmed to RT
temperatureheated to 50° C. for 4 hours
customThe solvents were removed in vacuo
dissolutionthe resulting residue was dissolved into EtOAc
washwashed with brine
dry with materialThe combined organic layers were dried (MgSO4)
customthe solvent was removed in vacuo

Sources & evidence

ORD record: ord-a141a06b15aa4fb9bf4be159a6c49aed
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07109354B2

Reaction notes

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