2-Bromobenzyl alcohol → 8-[2-(Hydroxymethyl)phenyl]-1,4-dioxaspiro[4.5]decan-8-ol

HRID 1809843ノート

反応式

HRID 1809843 の反応式
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[Li]CCCC.[CH2:15]1[O:25][C:18]2([CH2:23][CH2:22][C:21](=[O:24])[CH2:20][CH2:19]2)[O:17][CH2:16]1>C1COCC1>[OH:5][CH2:4][C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[C:21]1([OH:24])[CH2:22][CH2:23][C:18]2([O:25][CH2:15][CH2:16][O:17]2)[CH2:19][CH2:20]1

参加物

5

反応物 3

HCID 728502-Bromobenzyl alcoholHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 178418339Butyllithium

生成物 1

HCID 187600538-[2-(Hydroxymethyl)phenyl]-1,4-dioxaspiro[4.5]decan-8-ol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-4 °C

実験手順

To a solution of 2-bromobenzyl alcohol (3.0 g, 16 mmol) in THF (40 mL) cooled at −78° C. was added a 2.5 M solution of n-BuLi in hexanes (14.1 mL). The mixture was stirred at −4° C. for 1 hour and cooled back to −78° C. To it was added a solution of 1,4-cyclohexanedione mono-ethylene ketal (2.5 g, 16 mmol) in TIE (10 mL) over 15 minutes. Stirring was continued at −78° C. for 30 minutes and at −4° C. for 1 hour. The reaction was quenched by addition of a solution of NH4Cl in water. The resulting solution was extracted with EtOAc three times. The combined extract was washed with brine, dried over MgSO4 and concentrated. Purification on silica gel eluting with 5% MeOH/CH2Cl2 provided the title compound. MS calculated (M+H)+265. Found 287 (M+Na)+.

後処理

  1. temperaturecooled back to −78° C
  2. stirringStirring
  3. waitwas continued at −78° C. for 30 minutes and at −4° C. for 1 hour
  4. customThe reaction was quenched by addition of a solution of NH4Cl in water
  5. extractionThe resulting solution was extracted with EtOAc three times
  6. extractionThe combined extract
  7. washwas washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated
  10. customPurification on silica gel eluting with 5% MeOH/CH2Cl2

出典と根拠

ORDレコード
ord-8d5bc23c37034981801e7e8145bb2ea5
出典データセット
uspto-grants-2013_01
特許番号
US08362003B2

反応ノート

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