Lithium borohydride → 2-(4,5-Difluoro-2,3-dihydro-1H-inden-1-yl)ethanol

HRID 1178377ノート

反応式

HRID 1178377 の反応式
C([O:3][C:4](=O)[CH2:5][CH:6]1[C:14]2[C:9](=[C:10]([F:16])[C:11]([F:15])=[CH:12][CH:13]=2)[CH2:8][CH2:7]1)C.[Li+].[BH4-]>CCOC(C)=O.C1COCC1.CO.[Pd]>[F:16][C:10]1[C:11]([F:15])=[CH:12][CH:13]=[C:14]2[C:9]=1[CH2:8][CH2:7][CH:6]2[CH2:5][CH2:4][OH:3]

参加物

7

反応物 2

HCID 4148881Lithium borohydrideHCID 66998529(4,5-Difluoro-indan-1-yl)-acetic acid ethyl ester

生成物 1

HCID 219860842-(4,5-Difluoro-2,3-dihydro-1H-inden-1-yl)ethanol

試薬・触媒・溶媒 4

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of E- and Z-(4,5-difluoro-indan-1-ylidene)-acetic acid ethyl ester (Intermediate TWENTY-3) (1.1 g) in EtOAc (25 mL) was hydrogenated with 10% Pd/C (0.16 g) under H2 (balloon) at rt for 16 h. The mixture was filtered through a bed of Celite® and the filtrate was evaporated under vacuum. The ester, (4,5-difluoro-indan-1-yl)-acetic acid ethyl ester (1.1 g, 4.58 mmol) in THF (60 mL) and MeOH (1 mL) was treated with LiBH4 (0.21 g, 8.5 mmol) at 65° C. for 5 h. The mixture was cooled and THF was removed under vacuum. The solution was diluted with EtOAc and sat. NH4Cl. The layers were separated and the organic layer was dried over MgSO4 and filtered. After evaporation, the alcohol, 2-(4,5-difluoro-indan-1-yl)-ethanol (Intermediate TWENTY-4) was isolated as a clear, colorless oil, 1.7 g, (88%). Use, 2-(4,5-difluoro-indan-1-yl)-ethanol (Intermediate TWENTY-4) in Method SEVENTEEN produced 4-(4,5-difluoro-indan-1-ylmethyl)-1,3-dihydro-imidazole-2-thione (Compound 156).

後処理

  1. filtrationThe mixture was filtered through a bed of Celite®
  2. customthe filtrate was evaporated under vacuum
  3. temperatureThe mixture was cooled
  4. customTHF was removed under vacuum
  5. additionThe solution was diluted with EtOAc and sat. NH4Cl
  6. customThe layers were separated
  7. dry with materialthe organic layer was dried over MgSO4
  8. filtrationfiltered
  9. customAfter evaporation

出典と根拠

ORDレコード
ord-f893d5b3ec9b4d71b4b2b5613f1aabee
出典データセット
uspto-grants-2007_10
特許番号
US07276522B2

反応ノート

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