Hydrochloric Acid → HCID 18521038, compound

HRID 369529Notes

Reaction equation

HRID 369529 reaction equation
O.[OH-].[Li+].C[O:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)=[O:7].Cl>O.C1COCC1>[CH2:21]([O:20][C:17]1[CH:16]=[CH:15][C:14]([C:11]2[CH:12]=[CH:13][C:8]([C:6]([OH:7])=[O:5])=[CH:9][CH:10]=2)=[CH:19][CH:18]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 18521102HCID 18521102, compound

Product 1

HCID 18521038HCID 18521038, compoundYield 71.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (874 mg, 20.8 mmol) was added to a suspension of the ester 28a (2.00 g, 4.17 mmol), 50 ml water, and 200 ml THF. The mixture was refluxed for 48 hours and then was acidified with concentrated HCl. Water (150 ml) was added and the solution was cooled. The resulting tan precipitate was filtered and washed with water. The tan precipitate was dissolved in 100 ml hot THF and hexanes were added until the solution remained cloudy with stirring. After cooling, crystals were filtered to yield 1.4 g of a light yellow solid, and a second crop of crystals was isolated for a total yield of 1.67 g (86%). The product was used without further purification.

Workup

  1. temperatureThe mixture was refluxed for 48 hours
  2. temperaturethe solution was cooled
  3. filtrationThe resulting tan precipitate was filtered
  4. washwashed with water
  5. dissolutionThe tan precipitate was dissolved in 100 ml hot THF
  6. additionhexanes were added until the solution
  7. temperatureAfter cooling
  8. filtrationcrystals were filtered

Sources & evidence

ORD record
ord-6b3f76f8794348bcb46d4956664241cf
Source dataset
uspto-grants-2000_10
Patent number
US06139771

Reaction notes

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