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Triethylamine → HCID 69801944, compound

HRID 2307144
Notes
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Reaction equation

HRID 2307144 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:11])[CH2:9][CH3:10].[Si:13]([O:20][C:21]1[CH:26]=[C:25]([O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[CH:24]=[CH:23][C:22]=1[CH:35]1[CH2:40][CH2:39][CH:38]([CH2:41][OH:42])[CH2:37][CH2:36]1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]>CN(C)C1C=CN=CC=1.ClCCl>[C:8]([O:42][CH2:41][CH:38]1[CH2:37][CH2:36][CH:35]([C:22]2[CH:23]=[CH:24][C:25]([O:27][Si:28]([C:31]([CH3:33])([CH3:34])[CH3:32])([CH3:30])[CH3:29])=[CH:26][C:21]=2[O:20][Si:13]([C:16]([CH3:17])([CH3:18])[CH3:19])([CH3:15])[CH3:14])[CH2:40][CH2:39]1)(=[O:11])[CH2:9][CH3:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 54354272HCID 54354272, compound

Product 1

HCID 69801944HCID 69801944, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344
Dichloromethane
Solvent

Procedure

4-Dimethylaminopyridine (catalytic amount), triethylamine (68 μl) and propionyl chloride (42 μl) were added to a stirred solution of [4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl) cyclohexyl]methanol in anhydrous dichloromethane (3 ml) at room temperature under argon. After 16 hr, the reaction mixture was partitioned between water (10 ml) and ethyl acetate (20 ml). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×20 ml). The combined organic extracts were dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 1:19 v/v) to give the title compound as a yellow oil and a mixture of diastereoisomers (114 mg, 92%); δH(CDCl3) −0.04 (6H, s), 0.02 (6H, s), 0.96 (9H, s), 1.00 (9H, s), 1.08-1.18 (3H, m), 1.20-2.10 (9H, m), 2.24-2.40 (2H, m), 2.76-2.92 (1H, m), 3.94 (0.6H, d), 4.18 (0.4H, d), 6.26 (1H, m), 6.40 (1H, dd), 6.94-6.98 (1H, m).

Workup

  1. customthe reaction mixture was partitioned between water (10 ml) and ethyl acetate (20 ml)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (2×20 ml)
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 1:19 v/v)

Sources & evidence

ORD record
ord-6155e66480b64e7c8785bec66aa9600f
Source dataset
uspto-grants-2004_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06828460B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes