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

HRID 1015971노트

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HRID 1015971 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-4 °C

실험 절차

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 THF (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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-383c218d30f4401986d6cd8ed923c734
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07985730B2

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