Sodium Hydroxide → HCID 10697779, compound

HRID 651867Notes

Reaction equation

HRID 651867 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:18]=[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[I:27])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].CS(O[CH2:35][CH2:36][CH2:37][CH:38]=[CH2:39])(=O)=O>C1C=CC=CC=1.[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1>[CH2:20]([O:19][C:17]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([I:27])=[C:9]([N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:39][CH2:38][CH2:37][CH:36]=[CH2:35])[CH:18]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 10457640HCID 10457640, compoundHCID 11062723HCID 11062723, compound

Product 1

HCID 10697779HCID 10697779, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 159952Benzyltributylammonium chlorideCatalystHCID 241BenzeneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 80 (1.00 g, 2.11 mmol, 1 equiv) in benzene (100 mL) was treated with 50% w/v aqueous NaOH (20 mL). Benzyltributylammonium chloride (1.32 g, 4.22 mmol, 2 equiv) was added followed by 5-[(methanesulfonyl) oxy]-1-pentene (1.73 g, 10.53 mmol, 5 equiv). The resulting biphasic mixture was stirred vigorously at 25° C. for 12 h. The layers were allowed to separate and the aqueous portion was extracted with EtOAc (2×30 mL). The combined organic portions were washed with H2O (2×100 mL) and saturated aqueous NaCl (50 mL). Drying (MgSO4), filtration, and concentration was followed by flash chromatography (SiO2, 3.5×14 cm, 5% EtOAc-hexane) to furnish 81 (0.975 g, 1.15 g theoretical, 85%) as a pale yellow solid: mp 69-71° C.; 1H NMR (500 MHz, CDCl3) major rotamer δ 8.34-8.32 (m, 1H), 8.23-8.21 (m, 1H), 7.62-7.49 (m, 4H), 7.42-733 (m, 3H), 6.70 (s, 1H), 5.81-5.71 (m, 1H), 5.34-5.18 (m, 2H), 5.01-4.93 (m, 2H), 3.84 (ddd, J=17.5, 12.6, 7.6 Hz, 1H), 3.37-3.31 (m, 1H), 2.07-2.02 (m, 2H), 1.74-1.65 (m, 2H), 1.31 (s, 9H); 13C NMR (125 MHz, CDCl3) major rotamer δ 155.1, 154.0, 143.2, 137.9, 136.4, 135.4, 132.8, 128.7 (2C), 128.5, 128.2 (2C), 127.2, 126.2, 122.5, 115.0, 107.8, 95.1, 80.1, 70.3, 49.1, 31.3, 28.6, 28.3 (3C), 27.5; IR (film) νmax 3067, 3036, 2974, 2923, 1697, 1615, 1590 cm−1; FABHRMS (NBA-NaI) m/z 544.1337 (M+Na+, C27H30INO3 requires 544.1349).

Workup

  1. customto separate
  2. extractionthe aqueous portion was extracted with EtOAc (2×30 mL)
  3. washThe combined organic portions were washed with H2O (2×100 mL) and saturated aqueous NaCl (50 mL)
  4. customDrying
  5. filtration(MgSO4), filtration, and concentration

Sources & evidence

ORD record
ord-4ba697b2b53c4a62816ce58eb7529db0
Source dataset
uspto-grants-2001_08
Patent number
US06281354B1

Reaction notes

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