3-Chloro-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]benzaldehyde → 2-Chloro-4-ethenylphenol

HRID 1765644

반응식

HRID 1765644 반응식
[CH2:1]([Li])CCC.[Cl:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1[O:15][Si](C(C)(C)C)(C)C)[CH:10]=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[Cl:6][C:7]1[CH:8]=[C:9]([CH:10]=[CH2:1])[CH:12]=[CH:13][C:14]=1[OH:15]

참가 물질

5

반응물 2

HCID 220169343-Chloro-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]benzaldehydeHCID 178418339Butyllithium

생성물 1

HCID 208726142-Chloro-4-ethenylphenol

시약·촉매·용매 2

HCID 74505Methyltriphenyliphosphonium bromide촉매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

To a slurry of methyltriphenylphosphonium bromide (0.23 g) in dry THF (5 ml) under nitrogen at −78° C., n-butyl lithium (1.6M in hexanes, 0.37 ml) was added dropwise over 2 min. The mixture was allowed to warm to 0° C., stirred for 20 min, cooled to −78° C. and a solution of 3-chloro-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]benzaldehyde* (0.134 g) in dry THF (5 ml) added. The reaction mixture was allowed to reach room temperature overnight and quenched with saturated aqueous ammonium chloride. The resultant mixture was extracted with diethyl ether and the combined organic extracts were concentrated under reduced pressure. The residue was purified using SPE (silica, eluting with cyclohexane, followed by 5% to 25% ethyl acetate:cyclohexane) to give the title compound (0.049 g) as an oil. *Boukouvalas, J; Maltais, F; Lachance, N., Tetrahedron Lett. (1994), 35(43), 7897–900.

후처리

  1. temperaturecooled to −78° C.
  2. waitto reach room temperature overnight
  3. customquenched with saturated aqueous ammonium chloride
  4. extractionThe resultant mixture was extracted with diethyl ether
  5. concentrationthe combined organic extracts were concentrated under reduced pressure
  6. customThe residue was purified
  7. washSPE (silica, eluting with cyclohexane, followed by 5% to 25% ethyl acetate:cyclohexane)

출처 및 근거

ORD 기록
ord-1a3532fcd71647849172876a2b81938a
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07226929B2

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