Carbonate Ion → trans-2-[3-(2-Oxopropylsulfonyl)-4-n-propoxy-5-{3-(3-pyridyl)propoxy}phenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran

HRID 982470Notes

Reaction equation

HRID 982470 reaction equation
Br.Br[CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1.[O:12]=[C:13]([CH3:46])[CH2:14][S:15]([C:18]1[CH:19]=[C:20]([C@H:29]2[CH2:33][CH2:32][C@H:31]([C:34]3[CH:39]=[C:38]([O:40][CH3:41])[C:37]([O:42][CH3:43])=[C:36]([O:44][CH3:45])[CH:35]=3)[O:30]2)[CH:21]=[C:22]([OH:28])[C:23]=1[O:24][CH2:25][CH2:26][CH3:27])(=[O:17])=[O:16].C(=O)([O-])[O-]>CN(C=O)C>[O:12]=[C:13]([CH3:46])[CH2:14][S:15]([C:18]1[CH:19]=[C:20]([C@H:29]2[CH2:33][CH2:32][C@H:31]([C:34]3[CH:35]=[C:36]([O:44][CH3:45])[C:37]([O:42][CH3:43])=[C:38]([O:40][CH3:41])[CH:39]=3)[O:30]2)[CH:21]=[C:22]([O:28][CH2:3][CH2:4][CH2:5][C:6]2[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=2)[C:23]=1[O:24][CH2:25][CH2:26][CH3:27])(=[O:16])=[O:17]

Participants

5

Reactant 3

HCID 19660Carbonate IonHCID 127015693-(3-Bromopropyl)pyridine hydrobromideHCID 15078290trans-2-[3-(2-Oxopropylsulfonyl)-4-propoxy-5-hydroxyphenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran

Product 1

HCID 67906642trans-2-[3-(2-Oxopropylsulfonyl)-4-n-propoxy-5-{3-(3-pyridyl)propoxy}phenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

3-(3-Bromopropyl)pyridine hydrobromide (51 mg, 0.18 mmol) was added to a solution of trans-2-[3-(2-oxopropylsulfonyl)-4-n-propoxy-5-(2-hydroxy)phenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran (50.8 mg, 0.1 mmol) [Example 1, Step L] in DMF (2 mL) containing postassium carbonate (28 mg, 0.2 mmol), and the reaction mixture was heated at 70° C. for 1 h. The product was extracted with ethyl ether in the usualy way and purified by preparative TLC (hexane-ethyl acetate; 1:2, v/v) Rf 0.15; MS, m/z 628 (M+1)+. ; NMR (CDCl3) δ d 1.09 (t, J=7.5 Hz, CH2CH2CH3), 1.92 (m, CH2CH2CH3), 2.18 (m, CH2CH2CH2Pyr), 2.37 (s, CH2COCH3), 2.87 (t, CH2CH2CH2Pyr), 3.83 (s, OCH3 ), 3.88 (s, 2 OCH3), 4.08 (t, CH2CH2CH2Pyr), 4.18 (t, CH2CH2CH3), 4.48 (s, CH2CO), 5.13-5.27 (m, H-2 and H-5), 6.61 (s, 2 H, C5ArH).

Workup

  1. extractionThe product was extracted with ethyl ether in the usualy way
  2. custompurified by preparative TLC (hexane-ethyl acetate

Sources & evidence

ORD record
ord-17371b4b5dec4e8f957589f04ad31a04
Source dataset
uspto-grants-1991_02
Patent number
US04996203

Reaction notes

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