3-Hydroxyazetidine hydrochloride → (3,5-Di-tert-butyl-4-hydroxy-phenyl)-(3-hydroxy-azetidin-1-yl)-methanone

HRID 1766968ノート

反応式

HRID 1766968 の反応式
Cl.[NH:2]1[CH2:5][CH:4]([OH:6])[CH2:3]1.[C:7]([C:11]1[CH:12]=[C:13]([CH:17]=[C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:19]=1[OH:20])[C:14](Cl)=[O:15])([CH3:10])([CH3:9])[CH3:8]>[OH-].[Na+].C1COCC1>[C:21]([C:18]1[CH:17]=[C:13]([C:14]([N:2]2[CH2:5][CH:4]([OH:6])[CH2:3]2)=[O:15])[CH:12]=[C:11]([C:7]([CH3:10])([CH3:9])[CH3:8])[C:19]=1[OH:20])([CH3:24])([CH3:22])[CH3:23]

参加物

5

反応物 2

HCID 27592903-Hydroxyazetidine hydrochlorideHCID 37871873,5-Di-tert-butyl-4-hydroxybenzoyl chloride

生成物 1

HCID 11645178(3,5-Di-tert-butyl-4-hydroxy-phenyl)-(3-hydroxy-azetidin-1-yl)-methanone収率 30%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 14798Sodium Hydroxide溶媒

反応条件

温度
-5 °C

実験手順

Azetidin-3-ol hydrochloride (2 g, 18,3 mmoles) was dissolved in a 5% weight/weight (45 ml) of an aqueous solution of sodium hydroxide, the resulting solution cooled to −5° C. and under vigorous stirring 3,5-di-tert-butyl-4-hydroxy-benzoyl chloride (5,4 g, 20 mmoles) obtained according to step (a) dissolved in 8 ml of THF was added. Afterwards the cooling bath was removed, the reaction mixture warmed to room temperature (approximately 25° C.) and stirred for an additional hour under these conditions. The reaction mixture was then extracted several times with diethyl ether, the etherical phases combined, washed with water, dried with sodium sulfate and evaporated to dryness to obtain 1,9 g of the crude product, which is crystallized from ethyl acetate-petroleum ether. 1,6 g (30% of theoretical yield) of (3,5-di-tert-butyl-4-hydroxy-phenyl)-(3-hydroxy-azetidin-1-yl)-methanone were obtained in crystalline form.

後処理

  1. customobtained
  2. additionwas added
  3. customAfterwards the cooling bath was removed
  4. temperaturethe reaction mixture warmed to room temperature (approximately 25° C.)
  5. extractionThe reaction mixture was then extracted several times with diethyl ether
  6. washwashed with water
  7. dry with materialdried with sodium sulfate
  8. customevaporated to dryness
  9. customto obtain 1,9 g of the crude product, which
  10. customis crystallized from ethyl acetate-petroleum ether

出典と根拠

ORDレコード
ord-1279ba48fc04498ca542b43889c41df6
出典データセット
uspto-grants-2007_06
特許番号
US07232812B2

反応ノート

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