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

HRID 373570ノート

反応式

HRID 373570 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-052ec4539c664136b52a1b77bf52b8a7
出典データセット
uspto-grants-1992_11
特許番号
US05164387

反応ノート

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