Borane;tetrahydrofuran → HCID 18177940, compound

HRID 394951Notes

Reaction equation

HRID 394951 reaction equation
[CH3:1][C:2]1([CH3:23])[CH2:11][C:10]([CH3:13])([CH3:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:14]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:15](O)=[O:16])[CH:8]=2)[O:3]1.B.C1COCC1>C1COCC1>[CH3:1][C:2]1([CH3:23])[CH2:11][C:10]([CH3:12])([CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:14]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][OH:16])[CH:8]=2)[O:3]1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 18177822HCID 18177822, compound

Product 1

HCID 18177940HCID 18177940, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

0.8 g of (RS)-2-(2,2,4,4-tetramethyl-chroman-6-yl)-heptanoic acid were dissolved in 15 ml THF and treated dropwise, at 0° C., with 12.3 ml of 1M BH3.THF in THF. The mixture was stirred at 0° C. for two hours and then was quenched at 0° C. with careful addition of one portion of 15 ml of 3N HCl. The mixture was stirred at room temperature for 30 min. then was extracted with three portion of 75 ml of ethyl acetate. The combined organic extracts were dried over MgSO4 and concentrated in vacuo, giving a yellow oil. The product was purified by flash chromatography (SiO2, 10% ethyl acetate/hexanes), yielding 0.5 g of a pale yellow oil. 1H NMR (CDCl3): 7.06 (d, J=2.2 Hz, 1H), 6.90 (dd, J=8.3, 2.2 Hz, 1H), 6.75 (d, J=8.3 Hz, 1H), 3.72 (dd, J=10.7, 5.7 Hz, 1H), 3.64 (dd, J=10.7, 8.0 Hz, 1H), 2.75-2.65 (m, 1H), 1.82 (s, 2H), 1.70-1.45 (m, 2H), 1.35 (s, 6H), 1.34 (s, 6H), 1.30-1.15 (m, 6H), 0.83 (t, J=6.9 Hz, 3H).

Workup

  1. customwas quenched at 0° C. with careful addition of one portion of 15 ml of 3N HCl
  2. stirringThe mixture was stirred at room temperature for 30 min.
  3. extractionthen was extracted with three portion of 75 ml of ethyl acetate
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customgiving a yellow oil
  7. customThe product was purified by flash chromatography (SiO2, 10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-49e3cae2cc39457aa16e92f6e3d81eaf
Source dataset
uspto-grants-2003_08
Patent number
US06603012B2

Reaction notes

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