Benzyl Bromide → (1-((Benzyloxy)methyl)cyclobutyl)methanol

HRID 1180763ノート

反応式

HRID 1180763 の反応式
[OH:1][CH2:2][C:3]1([CH2:7][OH:8])[CH2:6][CH2:5][CH2:4]1.O1CCCC1.[H-].[Na+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O>[CH2:16]([O:1][CH2:2][C:3]1([CH2:7][OH:8])[CH2:6][CH2:5][CH2:4]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

6

反応物 4

HCID 7498Benzyl BromideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 4498243Cyclobutane-1,1-diyldimethanol

生成物 1

HCID 11458402(1-((Benzyloxy)methyl)cyclobutyl)methanol収率 86%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 8.0 g (69 mmol) of [1-(hydroxymethyl)cyclobutyl]methanol in 120 ml of a 1:1 mixture of tetrahydrofuran:N,N-dimethylformamide was added 3.30 g (69 mmol) of a 60% dispersion of sodium hydride in oil and the contents stirred for 30 min. 8.6 mL (72.4 mmol) of benzyl bromide was then added and the contents stirred for 2 h. The reaction was quenched with aqueous ammonium chloride followed by the addition of diethyl ether. The organic phase was isolated, dried using magnesium sulfate, and concentrated under vacuum to afford the crude product which was purified by silica gel chromatography using ethyl acetate:hexane (3:7) as the eluent to afford 12.0 g (86%) of {1-[(benzyloxy)methyl]cyclobutyl}methanol as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 7.33-7.25 (m, 5H), 4.49 (s, 2H), 3.66 (d, J=6 Hz, 2H), 3.52 (s, 2H), 2.53 (t, J=6 Hz, 1H), 1.91-1.73 (m, 6H). GC-MS m/z 207 (M+H).

後処理

  1. stirringthe contents stirred for 2 h
  2. customThe reaction was quenched with aqueous ammonium chloride
  3. additionfollowed by the addition of diethyl ether
  4. customThe organic phase was isolated
  5. customdried
  6. concentrationconcentrated under vacuum
  7. customto afford the crude product which
  8. customwas purified by silica gel chromatography

出典と根拠

ORDレコード
ord-1e1c4f77ea8740618f623f68238b27c9
出典データセット
uspto-grants-2007_10
特許番号
US07282512B2

反応ノート

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