Hydrochloric Acid → HCID 23172753, 화합물

HRID 1770309노트

반응식

HRID 1770309 반응식
Cl.C(OC(CBr)C#N)C1C=CC=CC=1.C(OC(CBr)C(N)=O)C1C=CC=CC=1.[CH2:29]([O:36][CH:37]([CH2:42]Br)[C:38]([O:40][CH3:41])=[O:39])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C1CN2C(=NCCC2)C1.C(=O)([O-])[O-].[K+].[K+]>CO.CCOCC.CCCCCC.O>[CH2:29]([O:36][C:37](=[CH2:42])[C:38]([O:40][CH3:41])=[O:39])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

참가 물질

10

반응물 5

HCID 313Hydrochloric AcidHCID 21253610HCID 21253610, 화합물HCID 212536202-Benzyloxy-3-bromopropionitrileHCID 21253638HCID 21253638, 화합물HCID 86748431HCID 86748431, 화합물

생성물 1

HCID 23172753HCID 23172753, 화합물

시약·촉매·용매 4

HCID 887Methanol용매HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8058Hexane용매

반응 조건

온도
-10 °C

실험 절차

A slow stream of hydrogen chloride gas was passed for 4 h through a solution of 2-benzyloxy-3-bromopropionitrile (16.75 g) in methanol (2.38 g) and ether (66 ml) which was maintained at -10° C. The mixture was allowed to stand at 5° C. overnight, and then ice was added in small portions to the mixture at 0° C. After 20 min of stirring, the mixture was poured into water and the product was extracted with ether, washed with water and aqueous sodium bicarbonate, and dried (MgSO4). After the solvent was removed, the crude product was recrystallized from ether/CH2Cl2 to afford, after a first crop of crystals of 2-benzyloxy-3-bromopropanamide, the required intermediate, methyl 2-benzyloxy-3-bromopropanoate. This bromoester was treated with DBN/potassium carbonate as described above to yield methyl α-benzyloxyacrylate, mp 44.5°-45.5° C. (from hexane); 1H NMR δ 3.80 (3H, s), 4.63 (1H, d, J 3 Hz), 4.83 (2H, s), 5.37 (1H, d, J 3 Hz), 7.33 (5H, s); IR 1740 cm-1. Ketals of alkyl pyruvates, prepared according to the directions in The Journal of Organic Chemistry, 1967, 32,1615, also may be converted to α-alkoxyacrylates by an acidic catalyst, as described in Chemische Berichte, 1911, 44, 3514.

후처리

  1. additionice was added in small portions to the mixture at 0° C
  2. extractionthe product was extracted with ether
  3. washwashed with water and aqueous sodium bicarbonate
  4. dry with materialdried (MgSO4)
  5. customAfter the solvent was removed
  6. customthe crude product was recrystallized from ether/CH2Cl2
  7. customto afford

출처 및 근거

ORD 기록
ord-1624827ff2ea4dc9b9ae462f6bb3dfe7
출처 데이터셋
uspto-grants-1995_01
특허 번호
US05385996

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