Ethanol, 1-bromo- → trans-2-[3-(3-Hydroxypropylsulfonyl)-4-n-propoxy-5-benzyloxyphenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran

HRID 982488Notes

Reaction equation

HRID 982488 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C@H:23]2[CH2:27][CH2:26][C@H:25]([C:28]3[CH:33]=[C:32]([O:34][CH3:35])[C:31]([O:36][CH3:37])=[C:30]([O:38][CH3:39])[CH:29]=3)[O:24]2)[CH:8]=[C:9]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]=1[O:11][CH2:12][CH2:13][CH3:14])(=[O:4])=[O:3].C([Li])CCC.Br[CH:46]([OH:48])[CH3:47]>C1COCC1>[OH:48][CH2:46][CH2:47][CH2:1][S:2]([C:5]1[CH:6]=[C:7]([C@H:23]2[CH2:27][CH2:26][C@H:25]([C:28]3[CH:33]=[C:32]([O:34][CH3:35])[C:31]([O:36][CH3:37])=[C:30]([O:38][CH3:39])[CH:29]=3)[O:24]2)[CH:8]=[C:9]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]=1[O:11][CH2:12][CH2:13][CH3:14])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 14202443Ethanol, 1-bromo-HCID 15078288racemic trans-2-(3-Methylsulfonyl-4-n-propoxy-5-benzyloxyphenyl)-5-(3,4,5-trimethoxyphenyl) tetrahydrofuranHCID 178418339Butyllithium

Product 1

HCID 67907127trans-2-[3-(3-Hydroxypropylsulfonyl)-4-n-propoxy-5-benzyloxyphenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

834 mg of trans-2-[3-methylsulfonyl-4-n-propoxy-5-benzyloxyphenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran dissolved in 8 ml of dry THF was cooled to -78° C. and to it was added 2 ml of n-butyllithium (1.6N solution in THF) in a nitrogen atmosphere. After 15 min. 140 mg of bromoethanol dissolved in 2 ml of THF was added to the reaction mixture. The yellow solution was warmed to room temperature and was quenched with a saturated NH4Cl solution. The title compound was obtained after workup and chromatography on silica gel: MS, m/z 600 M+ ; NMR (CDCl3, 200 MHz) δ 1.0 (t, OCH2CH2CH3), 1.82 (q, OCH2CH2CH3), 1.9-2.4(m, SO2CH2CH2CH2OH, H-4), 2.5(m, H-3), 3.58 (t, SO2CH2CH2CH2OH), 3.72(m, CH2OH), 3.86, 3.92(2s, 3 OCH3), 4.18 (t, OCH2CH2CH3), 5.18(s, OCH2Ar), 5.08-5.22 (m, H-2, H-5), 6.62(s, C5ArH), 7.28-7.54(m, ArH).

Workup

  1. additionwas added to the reaction mixture
  2. temperatureThe yellow solution was warmed to room temperature
  3. customwas quenched with a saturated NH4Cl solution

Sources & evidence

ORD record
ord-f48465d25f4a487cab01b0d77ebdd858
Source dataset
uspto-grants-1991_02
Patent number
US04996203

Reaction notes

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