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

HRID 275398

反応式

HRID 275398 の反応式
[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]

参加物

3

反応物 2

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

生成物 1

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

実験手順

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.

後処理

  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.)

出典と根拠

ORDレコード
ord-ae51ef06620140888809b2972abd90c6
出典データセット
uspto-grants-1995_02
特許番号
US05393764

関連ノート

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