Water → HCID 21242398, compound

HRID 1761733Notes

Reaction equation

HRID 1761733 reaction equation
[H-].[Na+].[CH2:3](Br)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:11]([O:27][C:28]([CH3:55])([CH3:54])[CH:29]([OH:53])[CH2:30][O:31]C(C1C=CC(OC)=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].O>CN(C)C=O>[CH2:11]([O:27][C:28]([CH3:54])([CH3:55])[CH:29]([O:53][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:30][OH:31])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 21242394HCID 21242394, compound

Product 1

HCID 21242398HCID 21242398, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 3.28 g of 50% sodium hydride in 40 ml of dimethylformamide containing 13.49 g of benzyl bromide was added dropwise a solution of 31.8 g of 3-(hexadecyloxy)-1-[(4-methoxyphenyl)diphenylmethoxy]-3-methyl-2-butanol in 50 ml of dimethylformamide over 45 minutes. The mixture was stirred overnight, then water was added and the mixture extracted with ether. The ether extract was dried and the solvent removed. The residue was stirred with 125 ml of methanol, 25 ml of tetrahydrofuran and 10 g of a strongly acidic ion exchange resin for 1.5 hours with warming, then filtered and the solvent removed. The residue was purified by HPLC, using hexane:ether (9:1), giving 12.14 g of the desired compound as a light yellow oil.

Workup

  1. extractionthe mixture extracted with ether
  2. extractionThe ether extract
  3. customwas dried
  4. customthe solvent removed
  5. stirringThe residue was stirred with 125 ml of methanol, 25 ml of tetrahydrofuran and 10 g of a strongly acidic ion exchange resin for 1.5 hours
  6. temperaturewith warming
  7. filtrationfiltered
  8. customthe solvent removed
  9. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-363478f39ef3439497c8ed11acafb11e
Source dataset
uspto-grants-1989_05
Patent number
US04827011

Reaction notes

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