Ethyl iodoacetate → HCID 67924050, compound

HRID 1493660Notes

Reaction equation

HRID 1493660 reaction equation
[C:1]([O:9][C@H:10]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C@@H:12]([CH2:13][CH2:14][C:15]3[C:16]4[C@:28]([CH3:36])([CH2:29][CH2:30][C:31]=32)[C@@H:19]([C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:18][C:17]=4[O:37][Si](C)(C)C)[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[CH2:43][C:44]([O:46][CH2:47][CH3:48])=[O:45].[F-].C([N+](C)(C)C)C1C=CC=CC=1>C1COCC1.CCCCCC>[C:1]([O:9][C@H:10]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C@@H:12]([CH2:13][CH2:14][C:15]3[C@@:16]4([CH2:43][C:44]([O:46][CH2:47][CH3:48])=[O:45])[C@:28]([CH3:36])([CH2:29][CH2:30][C:31]=32)[C@@H:19]([C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:18][C:17]4=[O:37])[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 12183Ethyl iodoacetateHCID 11062816N,N,N-Trimethyl(phenyl)methanaminium fluorideHCID 18645598HCID 18645598, compound

Product 1

HCID 67924050HCID 67924050, compoundYield 31.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-10 °C

Procedure

3β-benzoyloxy-15-trimethylsiloxy-5α-cholest-8,14-diene (1.93 g, 3.35 mmole) in THF (10 mL) and ethyl iodoacetate (0.79 mL, 6.7 mmole) was added at -10° C. to a mixture of benzyl trimethylammonium fluoride (850 mg, 5 mmole) in THF (15 mL). The mixture was stirred at -10° C. for 15 minutes and at ambient temperature for 30 minutes, diluted with hexane, filtered and the filtrate was concentrated. Using the workup described in Example 1(ii), 625 mg of 3β-benzoyloxy-14α-carbethoxymethyl-5α-cholest-8-en-15-one was obtained.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-18e19890ff01487884930320cff5bc3a
Source dataset
uspto-grants-1991_06
Patent number
US05023250

Reaction notes

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