Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester → HCID 10954617, compound

HRID 236428Notes

Reaction equation

HRID 236428 reaction equation
CC(OC[C:6]1[C:19]2[C:14](=CC=CC=2)[C:13]([CH2:20][O:21][C:22]([CH3:24])=[O:23])=C2C=1C=CC=C2)=O.C([O:27][C:28](=[O:30])[CH3:29])C.[CH3:31]CCCCC>CN(C1C=CN=CC=1)C>[C:22]([O:21][C@@H:20]([CH2:13][CH2:14][C@H:19]([O:30][C:28](=[O:27])[CH3:29])[CH3:6])[CH3:31])(=[O:23])[CH3:24]

Participants

4

Reactant 2

HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 21226206Ethyl acetate hexane

Product 1

HCID 10954617HCID 10954617, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

A solution of prolinol complex 10 (779 mg, 4.0 mmol) in THF (20 mL) was oxidized as above with ethylene glycol (0.44 mL, 7.9 mmol), 2M methanolic sodium hydroxide (12 mL, 24 mmol) and 30% H2O2 (2 mL, 20 mmol). Ether (50 mL) was added and the solution was washed with brine (2×10 mL). The aqueous phase was extracted with ether (2×10 mL). The combined organic layers were dried (K2CO3) and evaporated. Chromatography (ethyl acetate) of the residue afforded (R,R)-2,5-dihydroxyhexane (356 mg, 75% yield). The idol was acetylated with acetic anhdride (1.5 mL) and DMAP (30 mg) at 20° C. for 12 h. Standard workup followed by chromatography (ethylacetate/hexane, 1:9) gave (R,R)-2,5-diacetoxyhexane (482 mg, 80% yield). Bulb-to-bulb distillation gave pure diacetate.

Sources & evidence

ORD record
ord-2ec30518c8214b3c87693f8c8e85259a
Source dataset
uspto-grants-1987_02
Patent number
US04644075

Reaction notes

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