Hydrochloric Acid → HCID 86588413, compound

HRID 1353188Notes

Reaction equation

HRID 1353188 reaction equation
CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1.C([O:19][C:20](=O)/[CH:21]=[C:22](/[C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][C:33](/[C:36](/[CH3:48])=[CH:37]/[CH2:38][O:39][CH2:40][Si:41]([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:43])[CH3:42])=[CH:32][CH:31]=2)=[CH:26][CH:25]=1)\[CH3:23])C.Cl>C1COCC1.C(O)C>[Si:41]([CH2:40][O:39][CH2:38]/[CH:37]=[C:36](/[C:33]1[CH:32]=[CH:31][C:30]([C:27]2[CH:28]=[CH:29][C:24](/[C:22](/[CH3:23])=[CH:21]/[CH2:20][OH:19])=[CH:25][CH:26]=2)=[CH:35][CH:34]=1)\[CH3:48])([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:43])[CH3:42]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 14487Diisobutylaluminum hydrideHCID 86588414HCID 86588414, compound

Product 1

HCID 86588413HCID 86588413, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 1M solution of DIBAL-H in toluene (7.3 mL, 7.3 mmol) was, under a atmosphere of nitrogen, added dropwise at −70° C. over 20 min. to a stirred solution of (E)(E) 3-(4′-{3-[(tert-butyldimethylsilanyl)-methoxy]-1-methylpropenyl}-biphenyl-4-yl)-but-2-enoic acid ethyl ester (1.13 g, 2.43 mmol) in dry THF (25 mL). The mixture was stirred for 30 min. followed by 2 h at room temperature. Ethanol (1 mL) was carefully added, followed by 1N HCl (50 mL) and the resulting mixture extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with brine, dried (MgSO4), and evaporated to give 1.02 g (99%) of (E)(E) 3-(4′-{3-[(tert-butyldimethylsilanyl)-methoxy]-1-methylpropenyl}-biphenyl-4-yl)-but-2-en-1-ol.

Workup

  1. waitfollowed by 2 h at room temperature
  2. extractionthe resulting mixture extracted with ethyl acetate (2×50 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-1346e1f470f347f2a5688dfdbd85feb2
Source dataset
uspto-grants-2007_05
Patent number
US07220877B2

Reaction notes

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