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Chloroacetyl chloride → 2-Chloro-1-{1,4-dioxa-8-azaspiro[4.5]decan-8-yl}ethan-1-one

HRID 529855
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HRID 529855 반응식
[O:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[Cl:18][CH2:19][C:20](Cl)=[O:21]>ClCCl>[Cl:18][CH2:19][C:20]([N:8]1[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]1)=[O:21]
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참가 물질

5

반응물 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 674351,4-Dioxa-8-azaspiro(4.5)decane

생성물 1

HCID 438316402-Chloro-1-{1,4-dioxa-8-azaspiro[4.5]decan-8-yl}ethan-1-one수율 104.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

To a solution of 1,4-dioxa-8-azaspiro[4,5]decane (9.80 g, 67.1 mmol) in dichloromethane (150 mL) under nitrogen was added triethylamine (11.2 mL, 80.5 mmol. This was then cooled to 0° C. and to this was added dropwise with stirring 2-chloroacetyl chloride (6.53 mL, 80.5 mmol) in dichloromethane (50 mL) over 1 and a half hours. This was then stirred overnight warming to room temperature in the process. The reaction was then quenched by adding 1 N HCl (100 mL). This was then extracted with ethyl acetate and the ethyl acetate layers were dried with solid anhydrous magnesium sulfate powder, filtered and concentrated to give 2-Chloro-1-(1,4-dioxa-8-azaspiro[4,5]decan-8-yl)ethan-1-one as a brown oil (15.44 g). This was used without purification for the next step.

후처리

  1. temperaturewarming to room temperature in the process
  2. customThe reaction was then quenched
  3. additionby adding 1 N HCl (100 mL)
  4. extractionThis was then extracted with ethyl acetate
  5. dry with materialthe ethyl acetate layers were dried with solid anhydrous magnesium sulfate powder
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4e808dfb818947ce9e5b6078a8805022
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09346815B2

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