Water → HCID 59608877, 화합물

HRID 1047474노트

반응식

HRID 1047474 반응식
Br[C:2]1[C:10]([CH3:11])=[C:9]([CH3:12])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH:5]([CH3:15])[CH:6]2[O:13][CH3:14].[Li]CCCC.[CH2:21]1[O:23][CH2:22]1.O>C1COCC1>[CH3:14][O:13][CH:6]1[C:7]2[C:3](=[C:2]([CH2:21][CH2:22][OH:23])[C:10]([CH3:11])=[C:9]([CH3:12])[CH:8]=2)[CH2:4][CH:5]1[CH3:15]

참가 물질

6

반응물 4

HCID 962WaterHCID 6354Ethylene OxideHCID 59608908HCID 59608908, 화합물HCID 178418339Butyllithium

생성물 1

HCID 59608877HCID 59608877, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-110 °C

실험 절차

To a solution of 52.77 g (196.0 mmol) of 4-bromo-1-methoxy-2,5,6-trimethylindane in 300 ml of THF 156.8 ml of 2.5 M (392.1 mmol) n-BuLi in hexanes was added for 20 min at −80° C. This mixture was stirred for 40 min at this temperature, cooled to −110° C., and 17.27 g (392.1 mmol) of ethylene oxide was added by one portion at vigorous stirring. The resulting mixture was stirred for 12 h at room temperature, and then 10 ml of water was added. The organic layer was separated and evaporated to dryness. To the residue 200 ml of water was added, and the crude product was extracted with 3×100 ml of dichloromethane. The combined organic extract was dried over Na2SO4 and evaporated to dryness. The product was isolated by flash chromatography using short column with Silica Gel 60 (40-63 um, d 110 mm, l 90 mm; eluent: hexanes/ether=20/1). Yield 36.66 g (80%) of a ca. 1 to 1.7 mixture of two diastereomers.

후처리

  1. stirringThe resulting mixture was stirred for 12 h at room temperature
  2. customThe organic layer was separated
  3. customevaporated to dryness
  4. additionTo the residue 200 ml of water was added
  5. extractionthe crude product was extracted with 3×100 ml of dichloromethane
  6. extractionThe combined organic extract
  7. dry with materialwas dried over Na2SO4
  8. customevaporated to dryness
  9. customThe product was isolated by flash chromatography
  10. additionYield 36.66 g (80%) of a ca. 1 to 1.7 mixture of two diastereomers

출처 및 근거

ORD 기록
ord-7e3ab6773f2c436f849cd873516ca7c4
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569532B2

반응 노트

불러오는 중…