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 46013노트

반응식

HRID 46013 반응식
[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]

참가 물질

4

반응물 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 acetate2회

생성물 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}ethanol수율 81%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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:EtOAc:CH2Cl2 3:2:1+1.5% of Et3N) to provide 0.493 g (0.89 mmol, 81%) of 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 (sex, 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.

후처리

  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:EtOAc:CH2Cl2 3:2:1+1.5% of Et3N)

출처 및 근거

ORD 기록
ord-7d08260a1eab443092957330d5115ad7
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541625B2

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