3,6-Dioxabicyclo[3.1.0]hexane → HCID 67808836, compound

HRID 2260426Notes

Reaction equation

HRID 2260426 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([SH:15])[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])[CH3:3].[CH:16]12[O:21][CH:20]1[CH2:19][O:18][CH2:17]2>>[CH3:4][C:2]([C:5]1[CH:6]=[C:7]([S:15][C@@H:20]2[CH2:19][O:18][CH2:17][C@H:16]2[OH:21])[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:1])[CH3:3]

Participants

3

Reactant 2

HCID 675113,6-Dioxabicyclo[3.1.0]hexaneHCID 14795713HCID 14795713, compound

Product 1

HCID 67808836HCID 67808836, compound

Procedure

3,5-Bis(1,1-dimethylethyl)benzenethiol (0.0078 mole) and the title compound of Example 18 (0.0074 mole) are added to a degassed (Argon) solution of 50% sodium hydroxide (5 ml) and isopropyl alcohol (50 ml). The reaction is heated to reflux for 24 hours. The reaction is cooled to room temperature and poured into water (125 ml). The solution is made acidic with 1N hydrochloric acid and extracted 3 times with 100 ml of diethyl ether. The combined diethyl ether extracts are dried over anhydrous magnesium sulfate, filtered and concentrated with a rotary evaporator. The product is purified by silica gel chromatography.

Workup

  1. customa degassed (Argon) solution of 50% sodium hydroxide (5 ml) and isopropyl alcohol (50 ml)
  2. temperatureThe reaction is 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 are dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated with a rotary evaporator
  9. customThe product is purified by silica gel chromatography

Sources & evidence

ORD record
ord-5c119260370043f1be68567f80e3736c
Source dataset
uspto-grants-1995_12
Patent number
US05476944

Reaction notes

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