Imidazole → 5-Bromomethyl-5-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-1,3-dioxane

HRID 514622노트

반응식

HRID 514622 반응식
[Br:1][CH2:2][C:3]1([CH2:11][OH:12])[CH2:8][O:7][C:6]([CH3:10])([CH3:9])[O:5][CH2:4]1.N1C=CN=C1.[Cl-].[C:19]([SiH:23]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([CH3:22])([CH3:21])[CH3:20].[Cl-].[NH4+]>CN(C)C=O>[Br:1][CH2:2][C:3]1([CH2:11][O:12][Si:23]([C:19]([CH3:22])([CH3:21])[CH3:20])([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:4][O:5][C:6]([CH3:9])([CH3:10])[O:7][CH2:8]1

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 25517Ammonium ChlorideHCID 581652605-Bromomethyl-2,2-dimethyl-5-hydroxymethyl-1,3-dioxaneHCID 131727113Tert-butyldiphenyl silane chloride

생성물 1

HCID 903003725-Bromomethyl-5-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-1,3-dioxane수율 77.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
25 °C

실험 절차

1.1 g (4.6 mmol equivalents) of 5-bromomethyl-2,2-dimethyl-5-hydroxymethyl-1,3-dioxane was dissolved in 23 mL of dimethylformamide, 626 mg (9.2 mmol equivalents) of imidazole and 1.43 mL (5.5 mmol equivalents) of t-butyldiphenylsilane chloride were added thereto, and the mixture was stirred at room temperature (25° C.) for 5 hours. After completion of the reaction, a saturated aqueous solution of ammonium chloride was added dropwise, and the mixture was extracted with ethyl acetate three times. The combined ethyl acetate layers were washed with water and brine, then dried with anhydrous magnesium sulfate, and subsequently concentrated under vacuum. The obtained crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=20/1) to give 1.70 g (3.56 mmol equivalents) of 5-bromomethyl-5-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-1,3-dioxane.

후처리

  1. customAfter completion of the reaction
  2. extractionthe mixture was extracted with ethyl acetate three times
  3. washThe combined ethyl acetate layers were washed with water and brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationsubsequently concentrated under vacuum
  6. customThe obtained crude product
  7. customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=20/1)

출처 및 근거

ORD 기록
ord-a09efa332071447b9e3dec60cac1cd05
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09107964B2

반응 노트

불러오는 중…