tert-Butyldimethylsilyl chloride → HCID 131734420, compound

HRID 587907Notes

Reaction equation

HRID 587907 reaction equation
OC1C(C)=C(O)C=CC=1C=O.[Si](Cl)(C(C)(C)C)(C)C.C(N(CC)C(C)C)(C)C.[Si]([O:36][C:37]1[C:44]([CH3:45])=[C:43]([O:46][Si:47]([C:50]([CH3:53])([CH3:52])[CH3:51])([CH3:49])[CH3:48])[CH:42]=[CH:41][C:38]=1[CH:39]=[O:40])(C(C)(C)C)(C)C>>[Si:47]([O:46][C:43]1[CH:42]=[CH:41][C:38]([CH:39]=[O:40])=[C:37]([OH:36])[C:44]=1[CH3:45])([C:50]([CH3:53])([CH3:52])[CH3:51])([CH3:48])[CH3:49]

Participants

5

Reactant 4

HCID 28928tert-Butyldimethylsilyl chlorideHCID 803952,4-Dihydroxy-3-methylbenzaldehydeHCID 81531DiisopropylethylamineHCID 131734421HCID 131734421, compound

Product 1

HCID 131734420HCID 131734420, compound

Procedure

By following Example 2 procedure, 5.0 g of 2,4-Dihydroxy-3-methylbenzaldehyde was reacted with 4.95 g of tert-butyldimethylsilyl chloride and 2.15 g of N,N-diisopropylethylamine to get 7.91 g of crude title product containing 16.5% of 2,4-bis(tert-butyldimethylsilyloxy)-3-methylbenzaldehyde by GC. Crude product was purified by column chromatography to get the title compound as colorless liquid. IR (neat): 3280, 2956, 2932, 2888, 2859, 1646, 1622, 1582, 1493, 1425, 1388, 1360, 1325, 1296, 1249, 1171, 1103, 1021, 1007, 846, 798, 726, 679, 652, and 610 cm−1. 1H-NMR (CDCl3, 400 MHz): δ 11.56 (s, 1H, exch. with D2O, OH), 9.70 (s, 1H, CHO), 7.26 (d, J=8.4 MHz, 1H, aromatic H-6), 6.45 (d, J=8.4 Hz, 1H, aromatic H-5), 2.10 (s, 3H, ArCH3), 1.02 (s, 9H, Si-tert-Bu), 0.27 (s, 6H, SiMe2). 13C NMR (CDCl3, 100 MHz): δ 194.73 (CHO), 162.12 (C-2), 161.44 (C-4), 132.26 (C-6), 116.45 (C-1), 115.39 (C-3), 111.26 (C-5), 25.26 (CMe3), 18.29 (CMe3), 8.15 (ArCH3), 8.19 (SiMe2). Mass (EIMS): 266.26 (M), 265.19 (M−1).

Workup

  1. customto get 7.91 g of crude title product
  2. customCrude product was purified by column chromatography

Sources & evidence

ORD record
ord-0f5d64d0cf9c4e0390cfd318541fa433
Source dataset
uspto-grants-2016_01
Patent number
US09227948B2

Reaction notes

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