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Benzyl Alcohol → Benzyl 3-chloro-5-(tert-butyldimethylsilyloxy)benzoate

HRID 1698857
Notes
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Reaction equation

HRID 1698857 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH:10]=1)[C:5]([OH:7])=[O:6].C(Cl)(=O)C(Cl)=O.[CH2:25](O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(Cl)Cl.CN(C)C=O.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:13])[CH3:14])[CH:10]=1)[C:5]([O:7][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:6]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 244Benzyl AlcoholHCID 65578Oxalyl chlorideHCID 180074783-Chloro-5-(tert-butyldimethylsilyloxy)benzoic acid

Product 1

HCID 18322201Benzyl 3-chloro-5-(tert-butyldimethylsilyloxy)benzoate

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalyst
HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 6344DichloromethaneSolvent

Procedure

To a mixture of the acid 14 (3.80 g, 13.3 mmol) and oxalyl chloride (5.8 mL, 66 mmol) in methylene chloride (60 mL) was added ca. 0.05 mL of N,N-dimethylformamide as a catalyst. After stirring 1 hr at ambient temperature, the reaction was evaporated in vacuo, diluted with methylene chloride, and reacted with benzyl alcohol (1.38 mL, 13.3 mmol) and 4-(N,N-dimethylamino)pyridine (1.60 g, 13.3 mmol). After stirring 16 hrs at ambient temperature, the solution was washed with dilute aqueous HCl, dilute aqueous NaHCO3, and brine, dried over Na2SO4, and filtered. The filtrate was then evaporated in vacuo giving a quantitative yield of gold oil. 1H NMR (300 MHz, CDCl3) δ 7.64 (t, 1H, J=1.5 Hz), 7.45-7.28 (m, 6H), 7.02 (m, 1H), 5.35 (s, 2H), 0.98 (s, 9H), 0.22 (s, 6H).

Workup

  1. customthe reaction was evaporated in vacuo
  2. additiondiluted with methylene chloride
  3. stirringAfter stirring 16 hrs at ambient temperature
  4. washthe solution was washed with dilute aqueous HCl, dilute aqueous NaHCO3, and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customThe filtrate was then evaporated in vacuo

Sources & evidence

ORD record
ord-754f73e49fcf4dbfb824b26010042c95
Source dataset
uspto-grants-2002_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06344466B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes