Ammonium Chloride → 1,2,3,4,5,8,8a,9,10,10a-Decahydro-2,3-dimethylene-1,4-epoxy-8-hydroxy-anthracen-5-one

HRID 1154774Notes

Reaction equation

[CH2:1]=[C:2]1[C:15](=[CH2:16])[CH:14]2[O:17][CH:3]1[C:4]1[CH2:5][CH:6]3[CH:11]([CH2:12][C:13]=12)[C:10](=[O:18])[CH:9]=[CH:8][C:7]3=[O:19].[BH4-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>C(Cl)Cl.CO>[CH2:16]=[C:15]1[C:2](=[CH2:1])[CH:3]2[O:17][CH:14]1[C:13]1[CH2:12][CH:11]3[CH:6]([CH2:5][C:4]=12)[C:7](=[O:19])[CH:8]=[CH:9][CH:10]3[OH:18]

Participants

Conditions

Temperature: -70 °C

Procedure

A solution of 3.38 g of 1,2,3,4,8a,9,10,10a-octahydro-2,3-dimethylene-1,4-epoxyanthracene-5,8dione in 50 ml of methylene chloride and 50 ml of methanol was cooled to -70° C. and treated under nitrogen with 2.04 g of tetra-n-butylammonium borohydride in 10 ml of methylene chloride. The mixture was then stirred at -70° C. for 1.75 hours. After the addition of 100 ml of aqueous ammonium chloride solution, the solution was stirred for a further 1 hour. The phases were separated, the aqueous phase was extracted twice with 50 ml of methylene chloride each time and the combined organic phases were washed with two 100 ml portions of water and subsequently dried over magnesium sulphate. After concentration and recrystallisation, there were obtained 2.52 g (74%) of 1,2,3,4,5,8,8a,9,10,10a-decahydro-2,3-dimethylene-1,4-epoxy-8-hydroxy-anthracen-5-one of melting point 206°-207° C.

Workup

stirringthe solution was stirred for a further 1 hour
customThe phases were separated
extractionthe aqueous phase was extracted twice with 50 ml of methylene chloride each time
washthe combined organic phases were washed with two 100 ml portions of water
dry with materialsubsequently dried over magnesium sulphate
concentrationAfter concentration and recrystallisation

Sources & evidence

ORD record: ord-d1aa7d18196a47fc8ad5532cd85cacfd
Source dataset: uspto-grants-1981_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04298535

Reaction notes

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