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Diisopropylamine → Tert-butyl 6-triphenylmethyloxy-5-hydroxy-3-oxohexanoate

HRID 1594449
Notes
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Reaction equation

HRID 1594449 reaction equation
C(NC(C)C)(C)C.[Li]CCCC.[C:13]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])[CH3:14].[C:21]1([C:27]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[O:28][CH2:29][CH:30]([OH:36])[CH2:31][C:32](OC)=[O:33])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1.O>[C:21]1([C:27]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[O:28][CH2:29][CH:30]([OH:36])[CH2:31][C:32](=[O:33])[CH2:14][C:13]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 10908tert-Butyl acetateHCID 11245840Methyl 4-triphenylmethyloxy-3-hydroxybutyrateHCID 178418339Butyllithium

Product 1

HCID 19778647Tert-butyl 6-triphenylmethyloxy-5-hydroxy-3-oxohexanoate

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-15 °C

Procedure

125 mL of THF and 24 g of diisopropylamine were charged and cooled to −15° C. 168 mL of 1.2 N n-BuLi was added at −15 to −5° C. and was stirred for 30 minutes. 21.56 g of tert-butyl acetate in 45 mL of THF, which was pre-cooled to −45° C., was added maintaining the temperature between −45 to −25° C. for 60 minutes. The reaction mixture was cooled to −45° C. and 30 g of methyl 4-triphenylmethyloxy-3-hydroxybutyrate in THF was added over a period of 20 minutes and the stirring was continued at −25° C. for 90 minutes. Water was added and the layers were separated. The aqueous layer was extracted using EtOAc and the combined organic layers were washed with brine, water, dried and concentrated to give the title compound which was used as such for the next step.

Workup

  1. additionwas added
  2. temperaturemaintaining the temperature between −45 to −25° C. for 60 minutes
  3. temperatureThe reaction mixture was cooled to −45° C.
  4. waitthe stirring was continued at −25° C. for 90 minutes
  5. customthe layers were separated
  6. extractionThe aqueous layer was extracted
  7. washthe combined organic layers were washed with brine, water
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-04ab3f28f6c54b82810e23f863f9d1f3
Source dataset
uspto-grants-2007_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07301046B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes