Ethylene Glycol → 2-(1,3-Dioxolan-2-yl)-3-bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene

HRID 1836887ノート

反応式

HRID 1836887 の反応式
[CH:1]([C:3]1[C:12]([Br:13])=[CH:11][C:10]2[C:9]([CH3:15])([CH3:14])[CH2:8][CH2:7][C:6]([CH3:17])([CH3:16])[C:5]=2[CH:4]=1)=[O:2].[CH2:18](O)[CH2:19][OH:20].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[O:2]1[CH2:18][CH2:19][O:20][CH:1]1[C:3]1[C:12]([Br:13])=[CH:11][C:10]2[C:9]([CH3:15])([CH3:14])[CH2:8][CH2:7][C:6]([CH3:17])([CH3:16])[C:5]=2[CH:4]=1

参加物

5

反応物 3

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 177898873-Bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde

生成物 1

HCID 234989352-(1,3-Dioxolan-2-yl)-3-bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene収率 72%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

To a solution of 1.8 g (6.3 mmol) of 2-formyl-3-bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene in 70 mL of benzene was added 3.5 mL of ethylene glycol (63 mmol) followed by p-toluenesulfonic acid monohydrate (180 mg, 0.9 mmol). The reaction mixture was heated at reflux for about 3 hours and is then concentrated under reduced pressure. The residue was partitioned between ether and saturated sodium bicarbonate solution. The ether layer was washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by flash chromatography 1.4% ethyl acetate/) on a Biotage 40M SiO2 cartridge to afford 1.5 g (72%) of 2-(1,3-dioxolan-2-yl)-3-bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene as a crystalline solid.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for about 3 hours
  3. concentrationis then concentrated under reduced pressure
  4. customThe residue was partitioned between ether and saturated sodium bicarbonate solution
  5. washThe ether layer was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography 1.4% ethyl acetate/) on a Biotage 40M SiO2 cartridge

出典と根拠

ORDレコード
ord-7a2a360e899447d4969c686a5191a018
出典データセット
uspto-grants-2004_08
特許番号
US06777418B2

反応ノート

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