Diethyl Ether → 2-Hydroxy-3-(triphenylsilyl)-1-naphthaldehyde

HRID 453923Notes

Reaction equation

HRID 453923 reaction equation
[Li]C(C)(C)C.CCCCC.Br[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[C:14]([Si:22]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:13]=1[O:41]C.B(Br)(Br)Br.C(Cl)Cl.C[CH2:51][O:52]CC>O.CN(C=O)C>[OH:41][C:13]1[C:14]([Si:22]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:15][C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12]=1[CH:51]=[O:52]

Participants

9

Reactant 6

HCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 8003PentaneHCID 25134Boron tribromideHCID 86653240(4-Bromo-3-methoxy-2naphtyl)-triphenylsilaneHCID 178418306HCID 178418306, compound

Product 1

HCID 871931702-Hydroxy-3-(triphenylsilyl)-1-naphthaldehydeYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 16.1 mL of tert-BuLi 1.5 M in pentane (24.10 mmol) was added dropwise to a stirred solution of 6.02 g of (4-bromo-3-methoxy-2naphtyl)-triphenylsilane (12.05 mmol) in 50 mL of Et2O at −78° C. The reaction mixture was stirred during 1.5 h at a given temperature and 30 min at 0° C. followed by addition of 0.94 mL of DMF. The resultant mixture was stirred overnight at room temperature and diluted with 200 mL of water. The organic part was extracted with CH2Cl2 (3×50 mL). The combined organic extracts were dried over MgSO4. The resultant solution was transferred to a Schlenk flask under argon and a solution of 24.1 mL of BBr3 1M in CH2Cl2 (24.1 mmol) was added dropwise at −78° C. The reaction mixture was stirred overnight at room temperature, then carefully hydrolysed with 500 mL of water. The organic part was extracted with CH2Cl2 (3×50 mL). The combined organic extracts were dried over MgSO4, and evaporated. The crude residue was recrystallised from methanol and dried under vacuum to give 5.44 g of 1 (12.63 mmol) with a yield of 95%.

Workup

  1. extractionThe organic part was extracted with CH2Cl2 (3×50 mL)
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. customThe resultant solution was transferred to a Schlenk flask under argon
  4. stirringThe reaction mixture was stirred overnight at room temperature
  5. extractionThe organic part was extracted with CH2Cl2 (3×50 mL)
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. customevaporated
  8. customThe crude residue was recrystallised from methanol
  9. customdried under vacuum

Sources & evidence

ORD record
ord-93b42f3d020a48d8aec7b4c6fe3eec77
Source dataset
uspto-grants-2013_07
Patent number
US08492493B2

Reaction notes

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