Benzaldehyde → 3,4-dihydro-4,4-dimethyl-6-[(E)-alpha-methylstyryl]-2H-1-benzopyran

HRID 373570노트

반응식

HRID 373570 반응식
[Br-].[CH3:2][C:3]1([CH3:34])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH:13]([P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH3:14])[CH:11]=2)[O:6][CH2:5][CH2:4]1.[CH:35](=O)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.CO.O>C1OCCC1>[CH3:34][C:3]1([CH3:2])[C:12]2[CH:11]=[C:10](/[C:13](/[CH3:14])=[CH:35]/[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH:9]=[CH:8][C:7]=2[O:6][CH2:5][CH2:4]1

참가 물질

5

반응물 3

HCID 240BenzaldehydeHCID 199355281-(4,4-Dimethyl-6-chromanyl)ethyltriphenylphosphonium bromideHCID 22242641Methanol--water (1/1)

생성물 1

HCID 675909203,4-dihydro-4,4-dimethyl-6-[(E)-alpha-methylstyryl]-2H-1-benzopyran수율 19.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

16.5 g of [1-(4,4-dimethyl-6-chromanyl)ethyl]-triphenylphosphonium bromide and 3 g of benzaldehyde were heated under reflux in 100 ml of butylene oxide for 20 hours. The reaction mixture obtained was poured into a methanol/water mixture (6:4) and extracted with hexane. After drying and evaporating the organic phase the crude product was chromatographed (silica gel, eluting agent hexane) and recrystallized from hexane. There were obtained 1.5 g of 3,4-dihydro-4,4-dimethyl-6-[(E)-α-methylstyryl]-2H-1- benzopyran in the form of colorless crystals, melting point 64°-65° C.

후처리

  1. customThe reaction mixture obtained
  2. extractionextracted with hexane
  3. customAfter drying
  4. customevaporating the organic phase the crude product
  5. customwas chromatographed
  6. wash(silica gel, eluting agent hexane)
  7. customrecrystallized from hexane

출처 및 근거

ORD 기록
ord-052ec4539c664136b52a1b77bf52b8a7
출처 데이터셋
uspto-grants-1992_11
특허 번호
US05164387

반응 노트

불러오는 중…