7-(Pyridin-4-ylmethoxy)-1,2,3,4-tetrahydronaphthalen-1-one → 7-(Pyridin-4-ylmethoxy)-1,2,3,4-tetrahydronaphthalen-1-ol

HRID 2394326

反応式

HRID 2394326 の反応式
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[CH:18]=[C:17]3[C:12]([CH2:13][CH2:14][CH2:15][C:16]3=[O:19])=[CH:11][CH:10]=2)=[CH:3][CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1.C1(C)C=CC=CC=1>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[CH:18]=[C:17]3[C:12]([CH2:13][CH2:14][CH2:15][CH:16]3[OH:19])=[CH:11][CH:10]=2)=[CH:3][CH:2]=1

参加物

5

反応物 2

HCID 189732117-(Pyridin-4-ylmethoxy)-1,2,3,4-tetrahydronaphthalen-1-oneHCID 21225700Diisobutylaluminumhydride

生成物 1

HCID 189732197-(Pyridin-4-ylmethoxy)-1,2,3,4-tetrahydronaphthalen-1-ol収率 78.2%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of Compound 1 (16.41 g, 64.9 mmol) in tetrahydrofuran (75 mL) at 0° C. was added dropwise a 1M solution of diisobutylaluminum hydride in toluene (97.3 mL). After 1 hr, the reaction was quenched with aqueous potassium sodium tartrate and diluted with ethyl acetate followed by warming to room temperature. After stirring for an additional hour, the layers were separated and the aqueous phase was re-extracted with ethyl acetate (2×). The extracts were combined, washed with brine, dried over anh. magnesium sulfate, filtered and concentrated in vacuo. Chromatography of the residue on silica gel (elution with ethyl acetate) provided 12.96 g of Compound 2 as an oil which crystallized upon standing.

後処理

  1. customthe reaction was quenched with aqueous potassium sodium tartrate
  2. additiondiluted with ethyl acetate
  3. customthe layers were separated
  4. extractionthe aqueous phase was re-extracted with ethyl acetate (2×)
  5. washwashed with brine
  6. dry with materialdried over anh. magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-18649a9d73224d33be90767d3564d14d
出典データセット
uspto-grants-1998_09
特許番号
US05811434

関連ノート

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