3,6-Dioxabicyclo[3.1.0]hexane → trans-4-[[3,5-bis (1,1-Dimethylethyl)-4-hydroxyphenyl]thio]tetrahydro-3-furanol

HRID 275398

Reaction equation

HRID 275398 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

3

Reactant 2

HCID 675113,6-Dioxabicyclo[3.1.0]hexaneHCID 703702,6-Di-tert-butyl-4-mercaptophenol

Product 1

HCID 15224688trans-4-[[3,5-bis (1,1-Dimethylethyl)-4-hydroxyphenyl]thio]tetrahydro-3-furanol

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 1N 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

  1. customa degassed (Argon) solution of 50% sodium hydroxide (5 ml) and isopropyl alcohol (50 ml)
  2. temperatureThe reaction was heated
  3. temperatureto reflux for 24 hours
  4. additionpoured into water (125 ml)
  5. extractionextracted 3 times with 100 ml of diethyl ether
  6. dry with materialThe combined diethyl ether extracts were dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to an oily solid in a rotary evaporator
  9. customThe product was purified by silica gel chromatography
  10. customrecrystallized from hexane (m.p. ca. 104° C.)

Sources & evidence

ORD record
ord-ae51ef06620140888809b2972abd90c6
Source dataset
uspto-grants-1995_02
Patent number
US05393764

Linked notes

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