Sulfuric Acid → 10-Methoxy-6-oxaspiro[4.5]decane-7.8,9-triol
Reaction equation
[H-].[CH2:2]([Al+]CCCC)CCC.[C:11]([CH:14]([CH:16]([C:18]([O-:20])=[O:19])[OH:17])[OH:15])([O-:13])=O.[K+].[Na+].S(=O)(=O)(O)O.C(=O)([O-])[O-].[Ba+2].[C:33]1([CH3:39])[CH:38]=[CH:37][CH:36]=CC=1>O.C1COCC1>[CH3:2][O:13][CH:11]1[C:36]2([CH2:37][CH2:38][CH2:33][CH2:39]2)[O:20][CH:18]([OH:19])[CH:16]([OH:17])[CH:14]1[OH:15]Participants
Procedure
157 ml of a 1.5 M solution of dibutylaluminium hydride in toluene is added at −5° C. to a solution containing 56 g of the product of the previous stage and 300 ml of THF. Agitation is carried out at −3° C. for 1 hour. 1 liter of a 1 M solution of sodium potassium tartrate is added. Agitation is carried out for 15 minutes at ambient temperature. The reaction medium is extracted with an ethyl acetate-heptane 1-1 mixture followed by washing with water, salt water, drying and evaporating to dryness. The residue obtained is agitated at 70° C. in the presence of 150 ml of a solution of sulphuric acid 0.1 N and 150 ml of water for 2.5 hours. The reaction medium is cooled down to ambient temperature, barium carbonate is added, and agitation is carried out for 1 hour at ambient temperature followed by filtering and evaporating to dryness. 49 g of the sought product is obtained.
Workup
- waitAgitation is carried out for 15 minutes at ambient temperature
- extractionThe reaction medium is extracted with an ethyl acetate-heptane 1-1 mixture
- washby washing with water, salt water
- customdrying
- customevaporating to dryness
- customThe residue obtained
- waitagitation is carried out for 1 hour at ambient temperature
- filtrationby filtering
- customevaporating to dryness
Sources & evidence
- ORD record
- ord-62ee6cc2ac3b4e0abba356ca970f7e5c
- Source dataset
- uspto-grants-2002_07
- Patent number
- US06420538B1
Reaction notes
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