Sodium Bicarbonate → HCID 15235904, compound

HRID 2379541Notes

Reaction equation

[O:1]([CH2:9][P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].[Li]CCCC.[CH2:23](Br)[CH:24]=[C:25]([CH2:27][CH2:28][CH:29]=[C:30]([CH2:32][CH2:33][CH:34]=[C:35]([CH3:37])[CH3:36])[CH3:31])[CH3:26].C([O-])(O)=O.[Na+]>C1COCC1>[O:1]([CH:9]([P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])[CH2:23]/[CH:24]=[C:25](\[CH3:26])/[CH2:27][CH2:28]/[CH:29]=[C:30](\[CH3:31])/[CH2:32][CH2:33][CH:34]=[C:35]([CH3:37])[CH3:36])[Si:2]([C:5]([CH3:7])([CH3:6])[CH3:8])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: -78 °C

Procedure

To a stirred solution of the diethyl (t-butyldimethylsiloxy)methylphosphonate (562 mg, 2.0 mmol) in THF (5 ml) under argon at -78° C. was added n-BuLi (0.84 ml of a 2.5M solution in hexanes, 2.1 mmol) and the resulting mixture stirred at -78° C. for 15 min. Farnesyl bromide (0.542 ml, 2.0 mmol) was added to the mixture over 5 min and the solution stirred a further 1 hr at -78° C. and then allowed to warm to r.t. The reaction mixture was poured into saturated NaHCO3 solution and the organic solvent evaporated in vacuo, the residue was extracted into ethylacetate and washed with brine, dried (MgSO4) and concentrated in vacuo and the resulting oil chromatographed on silica gel eluted with ethylacetate:hexanes (3:7, v:v). to afford the title compound as an oil.

Workup

stirringthe solution stirred a further 1 hr at -78° C.
temperatureto warm to r.t
customthe organic solvent evaporated in vacuo
extractionthe residue was extracted into ethylacetate
washwashed with brine
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customthe resulting oil chromatographed on silica gel
washeluted with ethylacetate:hexanes (3:7, v:v)

Sources & evidence

ORD record: ord-c63bedfb778d473aa3f8b7f2d343ea19
Source dataset: uspto-grants-1994_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05362906

Reaction notes

Loading…