Ammonium Chloride → HCID 69927504, compound

HRID 392844Notes

Reaction equation

HRID 392844 reaction equation
COCN[C:5](=O)[C@@H:6]([C:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=1)[C@H:7]([O:21][CH3:22])[C@H:8]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[CH:9]=[CH2:10].[CH:30]([Mg]Br)=[CH2:31].[NH4+].[Cl-].C1COCC1.[OH2:41]>C1COCC1>[C:23]1([C@@H:6]([C@H:7]([O:21][CH3:22])[C@H:8]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)[CH:9]=[CH2:10])[C:5](=[O:41])[CH:30]=[CH2:31])[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 21881883Oxolane--water (1/1)HCID 69925229HCID 69925229, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 69927504HCID 69927504, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

279 mg (0.69 mmol) of (2S,3S,4R)-2-(cyclohex-1-enyl)-3-methoxy-4-p-methoxybenzyloxyhex-5-enoic acid methoxymethylamide are dissolved in THF (4 mL) and treated, at 0° C., with an excess of vinylmagnesium bromide (as a 1M solution in THF, 2.76 mL, 2.76 mmol, 4 equivalents). After addition, the mixture is allowed to warm to room temperature and is stirred overnight. An excess of saturated NH4Cl in a 1:1 THF/water mixture is then added. After extraction and evaporation of the solvents, the residue is chromatographed on silica (eluent (5/1 Cy/EtOAc)) to give 187 mg (73%) of (4S,5S,6R)-4-(cyclohex-1-enyl)-5-methoxy-6-p-methoxybenzyloxyocta-1,7-dien-3-one.

Workup

  1. additiontreated, at 0° C.
  2. additionAfter addition
  3. extractionAfter extraction and evaporation of the solvents
  4. customthe residue is chromatographed on silica (eluent (5/1 Cy/EtOAc))

Sources & evidence

ORD record
ord-f00c38efc8274f3ba7c0a18570fc2b77
Source dataset
uspto-grants-2004_10
Patent number
US06803382B2

Reaction notes

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