Sodium hydride → Bisfarnesyl ether

HRID 68203

Reaction equation

[H-].[Na+].[CH3:3][C:4]([CH3:18])=[CH:5][CH2:6][CH2:7]/[C:8](/[CH3:17])=[CH:9]/[CH2:10][CH2:11]/[C:12](/[CH3:16])=[CH:13]/[CH2:14][OH:15]>C1COCC1>[CH2:14]([O:15][CH2:14][CH:13]=[C:12]([CH2:11][CH2:10][CH:9]=[C:8]([CH2:7][CH2:6][CH:5]=[C:4]([CH3:3])[CH3:18])[CH3:17])[CH3:16])[CH:13]=[C:12]([CH2:11][CH2:10][CH:9]=[C:8]([CH2:7][CH2:6][CH:5]=[C:4]([CH3:18])[CH3:3])[CH3:17])[CH3:16]

Participants

Conditions

Temperature: 25 °C

Procedure

To 81 mg (2.03 mmole, 2 eq) of 60% sodium hydride (washed with anhydrous hexanes to remove mineral oil) in 1 mL of anhydrous THF under an argon atmosphere at 0° C., 228 mg (1.02 mmol) of trans,trans-farnesol in 1 mL of anhydrous THF was added. The mixture was stirred for 10 min, then 438 mg (1.53 mmol, 1.5 eq) of trans,trans-farnesol bromide was added in 0.5 ml of anhydrous THF. The mixture was stirred for 20 h and allowed to warm to 25° C. The reaction was quenched with 2 mL of 1M HCl, diluted with EtOAc, washed successively with water and brine and dried over anhydrous MgSO4. The crude product was chromatographed on silica gel F254 preparative TLC plates (Merck) in 1:10 EtOAc:hexanes to afford 174 mg (40%) of bisfarnesyl ether that had NMR and mass spectral data identical to that of material produced in enzymatic reactions (FIG. 7).

Workup

stirringThe mixture was stirred for 20 h
customThe reaction was quenched with 2 mL of 1M HCl
additiondiluted with EtOAc
washwashed successively with water and brine
dry with materialdried over anhydrous MgSO4
customThe crude product was chromatographed on silica gel F254 preparative TLC plates (Merck) in 1:10 EtOAc

Sources & evidence

ORD record: ord-9086d4653b814db0872f256be1da7b5e
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822187B1

Linked notes

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