3,6-Dioxabicyclo[3.1.0]hexane → trans-4-[[3,5-bis (1,1-Dimethylethyl)-4-hydroxyphenyl]thio]tetrahydro-3-furanol
Reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[C:9]([SH:11])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:4])[CH3:3].[CH:17]12[O:22][CH:21]1[CH2:20][O:19][CH2:18]2>>[CH3:4][C:2]([C:5]1[CH:10]=[C:9]([S:11][C@@H:21]2[CH2:20][O:19][CH2:18][C@H:17]2[OH:22])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:1])[CH3:3]Participants
Procedure
2,6-bis(1,1-Dimethylethyl)-4-mercaptophenol (1.85 g, 0.0078 mole) and the compound of Example 1 (0.64 g, 0.0074 mole) were added to a degassed (Argon) solution of 50% sodium hydroxide (5 ml) and isopropyl alcohol (50 ml). The reaction was heated to reflux for 24 hours. The reaction was cooled to room temperature and poured into water (125 ml). The solution was made acidic with 1 N hydrochloric acid and extracted 3 times with 100 ml of diethyl ether. The combined diethyl ether extracts were dried over anhydrous magnesium sulfate, filtered and concentrated to an oily solid in a rotary evaporator. The product was purified by silica gel chromatography and recrystallized from hexane (m.p. ca. 104° C.). The structure was supported by NMR and infrared spectroscopy and elemental analysis.
Workup
- customa degassed (Argon) solution of 50% sodium hydroxide (5 ml) and isopropyl alcohol (50 ml)
- temperatureThe reaction was heated
- temperatureto reflux for 24 hours
- additionpoured into water (125 ml)
- extractionextracted 3 times with 100 ml of diethyl ether
- dry with materialThe combined diethyl ether extracts were dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated to an oily solid in a rotary evaporator
- customThe product was purified by silica gel chromatography
- customrecrystallized from hexane (m.p. ca. 104° C.)
Sources & evidence
- ORD record
- ord-5a93c453aa1049849fc021a35456ac62
- Source dataset
- uspto-grants-1994_08
- Patent number
- US05334616
Reaction notes
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