Diethyl Ether → 2-Phenylethanol

HRID 604996ノート

反応式

HRID 604996 の反応式
[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

参加物

7

反応物 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 108687284-(((tert-Butyl(dimethyl)silyl)oxy)methyl)benzaldehydeHCID 178418336HCID 178418336、化合物

生成物 1

HCID 60542-Phenylethanol

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-40 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8c2f3d8158f844c48733b71d15a8af7d
出典データセット
uspto-grants-2011_03
特許番号
US07910561B2

反応ノート

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