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

HRID 1766968

반응식

HRID 1766968 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 14798Sodium Hydroxide용매

반응 조건

온도
-5 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1279ba48fc04498ca542b43889c41df6
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07232812B2

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