Hydrochloric Acid → (2SR,9aSR)-2-ALLYL-9a-BUTYL-7-HYDROXY-4-METHYL-1,2,9,9a-TETRAHYDRO-3H-FLUOREN-3-ONE

HRID 7872Notes

Reaction equation

[CH2:1]([CH:4]1[C:16](=[O:17])[C:15]([CH3:18])=[C:14]2[C:6]([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:7][C:8]3[C:13]2=[CH:12][CH:11]=[C:10]([O:19]COC)[CH:9]=3)[CH2:5]1)[CH:2]=[CH2:3].Cl>C1COCC1.CCOC(C)=O>[CH2:1]([CH:4]1[C:16](=[O:17])[C:15]([CH3:18])=[C:14]2[C:6]([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:7][C:8]3[C:13]2=[CH:12][CH:11]=[C:10]([OH:19])[CH:9]=3)[CH2:5]1)[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of (2SR,9aSR)-2-allyl-9a-butyl-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (5 mg, 0.015 mmol) in THF (0.5 mL) was treated with 6N HCl (0.5 mL) and the resulting solution was heated at 50° C. overnight. The mixture was diluted with EtOAc (30 mL), washed with 5% NaHCO3 and brine, dried over MgSO4, filtered, and evaporated under vacuum to a yellow oil. The crude product was purified by PLC on a 0.025×20×20 cm silica gel GF plate using 2:1 hexanes-EtOAc as developing solvent. The UV visible band at Rf 0.43-0.57 afforded (2SR,9aSR)-2-allyl-9a-butyl-7-hydroxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one as a gum.

Workup

washwashed with 5% NaHCO3 and brine
dry with materialdried over MgSO4
filtrationfiltered
customevaporated under vacuum to a yellow oil
customThe crude product was purified by PLC on a 0.025×20×20 cm silica gel GF plate

Sources & evidence

ORD record: ord-cf2f58d1d9b2468d8835b967eb71e56a
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087599B2

Reaction notes

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