Ethyl bromoacetate → HCID 69667031, compound

HRID 722140Notes

Reaction equation

Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[OH:8][C:9]1[CH:10]=[CH:11][C:12]2[CH2:19][CH:18]3[C:20](=[O:21])[CH:15]([CH2:16][CH2:17]3)[CH2:14][C:13]=2[CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH2:6]([O:5][C:3](=[O:4])[CH2:2][O:8][C:9]1[CH:22]=[C:13]2[C:12](=[CH:11][CH:10]=1)[CH2:19][CH:18]1[C:20](=[O:21])[CH:15]([CH2:16][CH2:17]1)[CH2:14]2)[CH3:7]

Participants

Conditions

Temperature: 90 °C

Procedure

Ethyl bromoacetate (8.01 g) was added to a stirred solution of [6S/R,9R/S]2-Hydroxy-5,6,7,8,9,10-hexahydro-6,9-methanobenzo[a][8]annulen-11-one (9.7 g; J. Org. Chem 1982, 47, 4329) and potassium carbonate (6.6 g) in dry DMF (150 mL). The reaction was warmed to 90° C. for 18 hours, cooled to room temperature, diluted with water (200 mL), and extracted into ether (4×100 mL). The organic extracts were washed with water (100 mL), brine (100 mL), dried over MgSO4, filtered and the solvent removed under reduced pressure. Flash chromatography over silica (200–400 mesh, 0–30% EtOAc/isoHexane) afforded (13-oxo-tricyclo[8.2.1.03,8]trideca-3,5,7-trien-5-yloxy)-acetic acid ethyl ester (11.07 g) 1H NMR (CDCl3 400 MHz) δ 1.28 (3H, m), 1.84 (2H, m), 2.58 (2H, m), 2.86 (4H, m), 4.15 (2H, m), 4.22 (2H, m), 4.59 (2H, s), 6.71 (1H, dd, J=8.0, 4.0 Hz), 6.80 (1H, d, J=4.0 Hz), 7.10 (1H, d, J=8.0 Hz).

Workup

temperaturecooled to room temperature
extractionextracted into ether (4×100 mL)
washThe organic extracts were washed with water (100 mL), brine (100 mL)
dry with materialdried over MgSO4
filtrationfiltered
customthe solvent removed under reduced pressure

Sources & evidence

ORD record: ord-50207c660e594126ac0df8fadffa9ec5
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138400B2

Reaction notes

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