Sodium Hydroxide → HCID 69964781, compound

HRID 1635581Notes

Reaction equation

[CH2:1]([O:3][CH:4]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH:19]=[CH:20][CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][CH:30]([O:36][CH2:37][CH3:38])[C:31]([O:33]CC)=[O:32])=[CH:25][CH:24]=2)=[CH:13][CH:12]=1)[C:5]([O:7]CC)=[O:6])[CH3:2].[OH-].[Na+]>C(O)C>[CH2:37]([O:36][CH:30]([CH2:29][C:26]1[CH:25]=[CH:24][C:23]([O:22][CH2:21][CH:20]=[CH:19][CH2:18][O:17][C:14]2[CH:15]=[CH:16][C:11]([CH2:10][CH:4]([O:3][CH2:1][CH3:2])[C:5]([OH:7])=[O:6])=[CH:12][CH:13]=2)=[CH:28][CH:27]=1)[C:31]([OH:33])=[O:32])[CH3:38]

Participants

Conditions

Temperature: 60 °C

Procedure

Ethyl 2-ethoxy-3-(4-(4-(4-(2-ethoxy-2-ethoxycarbonyl-ethyl)-phenyloxy)-but-2-enyloxy)-phenyl)-propionate (0.210 mmol, 109 mg) was dissolved in ethanol (7 ml) by heating to 60° C. 1M NaOH (2.3 ml) was added and the reaction mixture was stirred at 90° C. for 90 min. The reaction mixture was evaporated and 1 N HCl (6.5 ml) and methylene chloride (30 ml) was added to the residue. The organic phase was collected and the aqueous phase was further extracted with methylene chloride (2×25 ml). The combined organic phases were dried and evaporated to give the title compound in 87 mg (88%) yield. 1H-NMR δ (CDCl3) 9.55 (br. s, 2H), 7.17 (d, 4H), 6.80 (d, 4H), 5.91 (m, 2H), 4.65 (d, 4H), 4.05 (m, 2H), 3.70-3.57 (m, 2H), 3.50-3.35 (m, 2H), 3.10-2.90 (m, 4H), 1.21 (t, 6H).

Workup

customThe reaction mixture was evaporated
addition1 N HCl (6.5 ml) and methylene chloride (30 ml) was added to the residue
customThe organic phase was collected
extractionthe aqueous phase was further extracted with methylene chloride (2×25 ml)
customThe combined organic phases were dried
customevaporated

Sources & evidence

ORD record: ord-564cb0e1c32d4736b2bd64ad518b209f
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06509374B2

Reaction notes

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