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 1970222Notes

Reaction equation

HRID 1970222 reaction equation
[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]

Participants

4

Reactant 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×

Product 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}ethanolYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-daf61410840c4f428b58c679590b7f9a
Source dataset
uspto-grants-2013_04
Patent number
US08426649B2

Reaction notes

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