Diethyl Ether → HCID 53482763, compound

HRID 578724Notes

Reaction equation

HRID 578724 reaction equation
[CH3:1][C:2]([CH3:5])([O-:4])[CH3:3].[K+].[CH2:7]([C:22]([CH2:40][O:41][CH2:42][CH2:43][O:44][CH2:45][CH2:46][O:47][CH2:48][CH2:49][O:50][CH2:51][CH2:52][O:53][CH3:54])([CH2:38][OH:39])[CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH3:37])[O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21].[CH2:55]([O:57]CC)[CH3:56]>C1COCC1.[Cl-].[Na+].O>[CH2:23]([C:22]([CH2:40][O:41][CH2:42][CH2:43][O:44][CH2:45][CH2:46][O:47][CH2:48][CH2:49][O:50][CH2:51][CH2:52][O:53][CH3:54])([CH2:38][O:39][CH2:56][C:55]([O:4][C:2]([CH3:5])([CH3:3])[CH3:1])=[O:57])[CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])[O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH3:37]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 23665647Potassium tert-butoxideHCID 53482708HCID 53482708, compound

Product 1

HCID 53482763HCID 53482763, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Potassium tert-butoxide (32 mg, 0.28 mmol) was added to 4 (100 mg, 0.14 mmol) and tert-butyl-2-bromo acetate (105 mg, 0.54 mmol) in dry THF (3 ml). The reaction mixture was shaken for 30 min. Diethyl ether (10 ml and brine (5 ml) were added and the aqueous phase was extracted with ethyl acetate (3×20 ml). The combined organic phases were washed with brine and then dried with sodium sulfate. The volatile material was removed at reduced pressure and the crude product was purified by column chromatography (ethyl acetate/methanol 9:1), which gave 60 mg (52%) of 5. 1H-NMR (CDCl3); 3.91 (s, 2H), 3.66-3.52 (m, 48H), 3.51 (s, 2H), 3.45 (s, 6H), 3.37 (s, 9H), 1.46 (s, 9H).

Workup

  1. extractionthe aqueous phase was extracted with ethyl acetate (3×20 ml)
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried with sodium sulfate
  4. customThe volatile material was removed at reduced pressure
  5. customthe crude product was purified by column chromatography (ethyl acetate/methanol 9:1), which

Sources & evidence

ORD record
ord-1ab700dbf98b4cb6b0e185afcf4e0dff
Source dataset
uspto-grants-2015_05
Patent number
US09040637B2

Reaction notes

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