Hydrochloric Acid → HCID 76842371, 화합물

HRID 1296857노트

반응식

HRID 1296857 반응식
[CH3:1][C:2]([CH2:9][CH2:10][CH:11]=[C:12]([CH3:15])[CH:13]=[O:14])=[CH:3][CH2:4][O:5][C:6](=[O:8])[CH3:7].CC(=CC)C.P([O-])(O)(O)=[O:22].[Na+].Cl([O-])=O.[Na+].Cl>C(O)(C)(C)C.O.C(OCC)(=O)C>[C:6]([O:5][CH2:4][CH:3]=[C:2]([CH3:1])[CH2:9][CH2:10][CH:11]=[C:12]([CH3:15])[C:13]([OH:22])=[O:14])(=[O:8])[CH3:7]

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 566095533,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate

생성물 1

HCID 76842371HCID 76842371, 화합물수율 130.5%

시약·촉매·용매 3

HCID 962Water용매HCID 6386tert-Butanol용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of aldehyde 230a (19.5 g, 92.7 mmol) in 300 mL of tert-butyl alcohol was added 2-methyl-2-butene (98.0 mL, 925 mmol). To this was added a solution of sodium dihydrogen phosphate (44.5 g, 371 mmol) in 300 mL of water. Sodium chlorite (33.6 g, 371 mmol) was added in several portions. The resulting mixture was rapidly stirred overnight at room temperature. Ethyl acetate was added and the aqueous layer was acidified to pH 3 by addition of 1 M HCl. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (3×200 mL). The combined organic extracts were washed with brine, dried over MgSO4, and reduced to dryness in vacuo. The crude product (27.4 g, 121 mmol, >100% yield) was used in the next step without further purification: 1H NMR (500 MHz, CDCl3) δ: 6.84(t of q, J=7.25 Hz, J=1.50 Hz, 1H, ═CH), 5.34 (t of q, J=7.00 Hz, J=1.50 Hz, 1H, ═CH), 4.56 (d, J=7.00 Hz, 2H, —CH2O—), 2.31 (q, J=7.50 Hz, 2H, —CH2—), 2.15 (t, J=7.50 Hz, 2H, —CH2—), 2.03 (s, 3H, —CH3), 1.81 (s, 3H, —CH3), 1.70 (s, 3H, —CH3). LC/MS (ESI): m/z 249 [M+Na]+.

후처리

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with ethyl acetate (3×200 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4

출처 및 근거

ORD 기록
ord-d472dff24ee742689348a10d34805c13
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07247752B2

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