Sodium Hydroxide → 2-{2-[(9-Butoxy-5',5'-dimethyl-6,7-dihydrospiro-[dibenzo[a,e]cyclopropa[c][8]annulene-1,2'-[1,3]dioxan]-4-yl)oxy]ethoxy}ethanol

HRID 1970222ノート

反応式

HRID 1970222 の反応式
[OH-].[Na+].C([O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]2[C:23]3[C:24]4([O:29][CH2:28][C:27]([CH3:31])([CH3:30])[CH2:26][O:25]4)[C:22]=3[C:21]3[CH:32]=[CH:33][C:34]([O:36][CH2:37][CH2:38][CH2:39][CH3:40])=[CH:35][C:20]=3[CH2:19][CH2:18][C:17]=2[CH:41]=1)(=O)C>CO>[CH2:37]([O:36][C:34]1[CH:33]=[CH:32][C:21]2[C:22]3[C:24]4([O:29][CH2:28][C:27]([CH3:31])([CH3:30])[CH2:26][O:25]4)[C:23]=3[C:16]3[CH:15]=[CH:14][C:13]([O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][OH:6])=[CH:41][C:17]=3[CH2:18][CH2:19][C:20]=2[CH:35]=1)[CH2:38][CH2:39][CH3:40]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 667791322-{2-[(9-Butoxy-5',5'-dimethyl-6,7-dihydrospiro-[dibenzo[a,e]cyclopropa[c][8] annulene-1,2'-[1,3]dioxan]-4-yl)oxy]ethoxy}ethyl acetate2 回

生成物 1

HCID 667789362-{2-[(9-Butoxy-5',5'-dimethyl-6,7-dihydrospiro-[dibenzo[a,e]cyclopropa[c][8]annulene-1,2'-[1,3]dioxan]-4-yl)oxy]ethoxy}ethanol収率 81%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of NaOH (1.2 mL, 1.2 mmol, 1 M aqueous solution) was added to solution of acetate 10 (0.593 g, 1.11 mmol) in MeOH:THF (10:3 mL) at room temperature, and the reaction mixture was stirred for 30 minutes at room temperature. The reaction mixture was partially concentrated under reduced pressure, diluted with EtOAc (approximately 25 mL) and water (approximately 10 mL), the organic layer was separated, washed with brine, and dried over anhydrous MgSO4. Solvents were evaporated under reduced pressure, and the residue was separated by chromatography (Hex:ExOAc:CH2Cl2 3:2:1+1.5% of Et3N) to provide 0.493 g (0.89 mmol, 81%) of an alcohol 11 as slightly yellow oil that crystallizes on standing. 1H NMR: 7.65 (dd, J=8.4, 2.4 Hz, 2 H), 6.92-6.82 (m, 4 H), 4.18 (t, J=4.4 Hz, 2 H), 4.04 (t, J=6.4 Hz, 2 H), 3.92 (m, 4 H), 3.88 (t, J=4.4 Hz, 2 H), 3.77 (t, J=4.4 Hz, 2 H), 3.68 (t, J=4.4 Hz, 2 H), 3.24 (d, J=10.8 Hz, 2 H), 2.41 (d, J=10.8 Hz, 2 H), 1.76 (p, J=7.2 Hz, 2 H), 1.50 (six, J=7.6 Hz, 2 H), 1.21 (s, 3 H), 1.19 (s, 3 H), 0.99 (t, J=7.2 Hz, 3 H); 13C NMR: 159.8, 159.2, 147.4, 131.84, 131.75, 131.67, 131.57, 124.4, 123.6, 119.8, 119.1, 116.3, 116.2, 112.2, 84.1, 79.4, 72.8, 69.8, 68.0, 76.7, 62.0, 37.1, 31.5, 30.8, 22.9, 19.4, 14.2.

後処理

  1. concentrationThe reaction mixture was partially concentrated under reduced pressure
  2. additiondiluted with EtOAc (approximately 25 mL) and water (approximately 10 mL)
  3. customthe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. customSolvents were evaporated under reduced pressure
  7. customthe residue was separated by chromatography (Hex:ExOAc:CH2Cl2 3:2:1+1.5% of Et3N)

出典と根拠

ORDレコード
ord-daf61410840c4f428b58c679590b7f9a
出典データセット
uspto-grants-2013_04
特許番号
US08426649B2

反応ノート

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