Pinacol → HCID 178428379, compound

HRID 1014755Notes

Reaction equation

HRID 1014755 reaction equation
C[N:2]([C-:4]1[CH:8]=[CH:7][CH:6]=[CH:5]1)C.[CH-:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1.[Fe+2:14].B(F)(F)F.CCO[CH2:22][CH3:23].[Li]CCCC.[B:29](OCC)(OCC)OCC.[OH:39][C:40]([C:43]([OH:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41]>C1COCC1>[CH3:6][C:7]1[C:22]([CH3:23])=[C:5]([B:29]2[O:46][C:43]([CH3:45])([CH3:44])[C:40]([CH3:42])([CH3:41])[O:39]2)[C-:4]([NH2:2])[CH:8]=1.[CH-:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1.[Fe+2:14]

Participants

7

Reactant 5

HCID 6425PinacolHCID 8000Boron trifluoride etherateHCID 9009Triethyl borateHCID 129678476cyclopenta-1,3-diene;N,N-dimethylcyclopenta-2,4-dien-1-amine;iron(2+)HCID 178418339Butyllithium

Product 1

HCID 178428379HCID 178428379, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 11 (229 mg, 1.0 mmol) in THF (10 mL) was sequentially treated with BF3.OEt2 (0.13 mL, 1.05 mmol), n-BuLi (0.55 mL, 2.00 M, 1.10 mmol) and B(OEt)3 (0.20 mL, 1.20 mmol). Standard workup gave the extract, to which was added pinacol (138 mg, 1.10 mmol) and stirred at room temperature for 5 min. Concentration of the mixture under reduced pressure and column chromatography (basic alumina, hexanes) gave 12e (298 mg, 84%) as an orange oil that solidified on standing; mp 75-76° C. (pentane); IR (KBr) vmax 3090, 2978, 2833, 2785, 1141, 1077 cm−1; 1H NMR (300 MHz, acetone-d6) 4.18 (s, 5H), 4.16 (s, 1H), 4.08 (s, 2H), 2.65 (s, 6H), 1.32 (s, 12H) ppm; 13C NMR (75.5 MHz, acetone-d6) 119.6, 82.7, 71.9, 68.3, 67.5, 66.0, 60.1, 43.7, 24.4, 24.1 ppm; EIMS [m/z (%)] 355 (M+, 100), 255 (15), 121 (20); HRMS (EI) calcd for C18H26BNO256Fe: 355.1406. Found 355.1411. Anal. Calcd for C18H26BNO2Fe: C, 60.89; H, 7.38. Found: C, 60.96; H, 7.48.

Workup

  1. customStandard workup gave the extract

Sources & evidence

ORD record
ord-745ee189bdf546568a18e4cadfdd4a4c
Source dataset
uspto-grants-2011_07
Patent number
US07982064B2

Reaction notes

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