Diethyl Ether → 2-Phenylethanol

HRID 604996노트

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HRID 604996 반응식
[Si](OC[C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=1)(C(C)(C)C)(C)C.C([Mg]Cl)C1C=CC=CC=1.[CH2:27]([O:29]CC)C.[Cl-].[NH4+]>O1CCCC1.O>[C:13]1([CH2:14][CH2:27][OH:29])[CH:12]=[CH:11][CH:10]=[CH:17][CH:16]=1

참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 108687284-(((tert-Butyl(dimethyl)silyl)oxy)methyl)benzaldehydeHCID 178418336HCID 178418336, 화합물

생성물 1

HCID 60542-Phenylethanol

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-40 °C

실험 절차

4-(t-Butyldimethylsilyloxymethyl)benzaldehyde (Synthesis (1995), 12, 1529-33) (6.65 gm, 26 mmol) was dissolved in dry tetrahydrofuran (50 mL) and the solution cooled to −40° C. Benzyl magnesium chloride in diethyl ether (1 M, 35 mL, 35 mmol) was added slowly. The reaction was allowed to warm to 0° C. over three hours. The reaction was then quenched by the addition of ammonium chloride (2.3 gm, 43 mmol) in water (60 mL). The product was extracted into diethyl ether, washed with NaHCO3 solution, dried (over Na2SO4), and filtered. The solution was evaporated to give 1-[4-t-butyldimethylsilyloxymethyl)-phenyl]-2-phenylethanol as an oil which was used as is. 1H-NMR (500 MHz, CDCl3): δ 7.19-7.34 (9H, m), 4.90 (1H, dd, J=4.9, 8.3 Hz), 4.75 (2H, s), 2.98-3.07 (2H, dt), 0.95 (6H, s), 0.11 (9H, s).

후처리

  1. temperatureto warm to 0° C. over three hours
  2. extractionThe product was extracted into diethyl ether
  3. washwashed with NaHCO3 solution
  4. dry with materialdried (over Na2SO4)
  5. filtrationfiltered
  6. customThe solution was evaporated

출처 및 근거

ORD 기록
ord-8c2f3d8158f844c48733b71d15a8af7d
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910561B2

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