Sodium Hydroxide → HCID 10067865, compound

HRID 490040Notes

Reaction equation

HRID 490040 reaction equation
[OH-].[Na+].C([O:6][C:7](=[O:33])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[C:15]2[C:20]([O:21][C:22]3[C:27]=1[CH:26]=[CH:25][C:24](=[O:28])[CH:23]=3)=[CH:19][C:18]([O:29][CH2:30][CH:31]=[CH2:32])=[CH:17][CH:16]=2)C=C>CO>[OH:28][C:24]1[CH:25]=[CH:26][C:27]2[C:14]3([C:9]4[C:8](=[CH:13][CH:12]=[CH:11][CH:10]=4)[C:7](=[O:6])[O:33]3)[C:15]3[C:20]([O:21][C:22]=2[CH:23]=1)=[CH:19][C:18]([O:29][CH2:30][CH:31]=[CH2:32])=[CH:17][CH:16]=3

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15196186HCID 15196186, compound

Product 1

HCID 10067865HCID 10067865, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaOH (20 mL, 1.0 M, 20.0 mmol) was added to a solution of 17 (0.40 g, 0.97 mmol) in methanol (60 mL). The resulting mixture was stirred for 2 h at room temperature. The mixture was concentrated, diluted with ethyl acetate, washed with 10% NaHCO3, brine, dried with anhydrous Na2SO4, and evaporated. The residue was purified by column chromatography (ethyl acetate/hexane=1:1) to give 18 as a yellow solid (0.23 g, 65%). TLC (ethyl acetate/hexane, 3:1): Rf=0.6. mp 204° C. 1H NMR (CDCl3/CD3OD, 500 MHz) δ 4.58 (d, J=5.0 Hz, 2H, CH2), 5.32 (d, J=10.5 Hz, 1H, CH), 5.43 (d, J=17.5 Hz, 1H, CH), 6.04 (m, 1H, CH), 6.62 (m, 4H), 6.74 (s, 1H), 6.80 (s, 1H), 7.20 (d, J=7.5 Hz, 1H), 7.65 (t, J=7.5 Hz, 1H), 7.71 (t, J=7.5 Hz, 1H), 8.01 (d, J=7.5 Hz, 1H). 13C NMR (CDCl3/CD3OD, 125 MHz) δ 69.00, 101.71, 102.73, 109.90, 111.21, 111.94, 112.42, 117.89, 124.04, 124.80, 126.69, 128.88, 128.95, 129.72, 132.51, 135.16, 152.56, 160.28, 170.26. ESIMS calcd for C23H17O5 [M+H]+ 373.1. Found 373.2.

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with ethyl acetate
  3. washwashed with 10% NaHCO3, brine
  4. dry with materialdried with anhydrous Na2SO4
  5. customevaporated
  6. customThe residue was purified by column chromatography (ethyl acetate/hexane=1:1)

Sources & evidence

ORD record
ord-34f54b7c0c0c445180fad8197ab79505
Source dataset
uspto-grants-2009_05
Patent number
US07527934B2

Reaction notes

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