HCID 86760717, compound → HCID 86760716, compound

HRID 747818Notes

Reaction equation

HRID 747818 reaction equation
[CH:1]12[CH2:9][CH:5]([C:6]1([CH3:8])[CH3:7])C[CH2:3][CH:2]2C.[C:11]([OH:14])(=[O:13])[CH3:12].[O:15](O)O>C(Cl)(Cl)Cl>[C:11]([OH:14])(=[O:13])[CH3:12].[C:5]12([OH:15])[CH2:9][CH:1]([C:6]1([CH3:8])[CH3:7])[CH2:2][CH2:3][C:11]2([OH:14])[CH3:12]

Participants

3

Reactant 1

HCID 86760717HCID 86760717, compound

Product 1

HCID 86760716HCID 86760716, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The mixture was extracted with 50% EtOAc/hexanes two times. The combined organic extract was washed with 10% NaHSO3 solution and water, dried over anhydrous Na2SO4 and concentrated to afford the crude product as a tan oil (2.85 g). The pinanediol acetate 3 was purified by silica gel chromatography, eluting with 5˜50% EtOAc/hex, to yield a nearly colorless oil (2.03 g, 84%) containing a small amount of a less polar pinane-keto-alcohol acetate byproduct. IR (CHCl3): 3450, 3000, 2927, 2870, 1730, 1475, 1455, 1388, 1370, 1230, 1128, 1042, and 605 cm−1. 1HNMR (400 MHz, CDCl3): δ 4.26-4.38 (m, 2H), 4.03-4.09 (m, 1H), 3.15 (s, 1H, OH), 2.89 (d, J=6.2 Hz, 1H, OH), 2.46-2.54 (m, 1H), 2.18-2.26 (m, 1H), 2.10 (t, J=5.8 Hz, 1H), 2.06(s, 3H), 1.92-2.05 (m, 2H), 1.79-1.87 (m, 1H), 1.63-1.70 (m, 1H), 1.38 (d, J=10.4 Hz, 1H), 1.27 (s, 3H), 0.94 (s, 3H).

Sources & evidence

ORD record
ord-40ed4f6a282246a7a1e4eb71ce2614ad
Source dataset
uspto-grants-2008_07
Patent number
US07399645B2

Reaction notes

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