Sodium borohydride → HCID 21877258, compound

HRID 1816823Notes

Reaction equation

HRID 1816823 reaction equation
BrC1C=CC(O)=C(OC)C=1C=O.[Br:13][C:14]1[C:28]([CH2:29][O:30]CC)=[CH:27][C:17]([O:18][CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])=[C:16]([O:33][CH3:34])[CH:15]=1.[BH4-].[Na+].[Br:37][C:38]1[CH:45]=[C:44]([O:46][CH3:47])[C:43]([O:48][CH2:49][O:50][CH2:51][CH2:52][Si:53]([CH3:56])([CH3:55])[CH3:54])=[CH:42][C:39]=1[CH:40]=[O:41]>CO.O>[Br:13][C:14]1[CH:15]=[C:16]([O:33][CH3:34])[C:17]([O:18][CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:24])([CH3:26])[CH3:25])=[CH:27][C:28]=1[CH:29]=[O:30].[Br:37][C:38]1[CH:45]=[C:44]([O:46][CH3:47])[C:43]([O:48][CH2:49][O:50][CH2:51][CH2:52][Si:53]([CH3:55])([CH3:54])[CH3:56])=[CH:42][C:39]=1[CH2:40][OH:41]

Participants

8

Reactant 4

HCID 4311764Sodium borohydrideHCID 10585585HCID 10585585, compoundHCID 21877258HCID 21877258, compoundHCID 21877322HCID 21877322, compound

Product 2

HCID 21877258HCID 21877258, compoundYield 79%HCID 22486246HCID 22486246, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The starting material was prepared as follows: 2-Bromo-4-methoxy-5-(2-trimethylsilanyl-ethoxymethoxy)-benzaldehyde was prepared in 79% yield by the substitution of 4-bromo-3-formyl-2-methoxy-phenol (Hazlet et. al., J. Org. Chem., 27, 3253-55 (1962)) in the procedure described in Example 24(a), step(vi). 1H NMR (300 MHz, CDCl3)δ 10.16(s, 1H), 7.68 (s, 1H), 7.07 (s, 1H), 5.28 (s, 2H), 3.94 (s, 3H), 3.77 (t, 2H, J=8.4 Hz), 0.94 (t, 2H, J=8.4 Hz), −0.03 (s, 9H). Preparation of [2-(4-Bromo-5-ethoxymethyl-2-methoxy-phenoxymethoxy)-ethyl]-trimethyl-silane: Sodium borohydride (275 mg, 7.2 mmol) was added in portions over 10 min to a solution of 2-bromo-4-methoxy-5-(2-trimethylsilanyl-ethoxymethoxy)-benzaldehyde (1.3 g, 3.6 mmol) in MeOH (20 mL) at 0° C. After 30 min, the reaction was diluted with H2O (40 mL) and extracted with EtOAc (2×30 mL). Organics were washed with brine (30 mL), dried (Na2SO4) and concentrated in vacuo to give 1.31 g of [2-bromo-4-methoxy-5-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-methanol as a clear oil. 1H NMR (300 MHz, CDCl3) δ 7.29 (s, 1H), 7.05 (s, 1H), 5.27 (s, 2H), 4.66 (d, 2H, J=6.6 Hz), 3.87 (s, 3H), 3.79 (t, 2H, J=8.4 Hz), 1.92 (t, 1H, J=6.6 Hz), 0.96 (t, 2H, J=8.4 Hz), 0.01 (s, 9H).

Workup

  1. customThe starting material was prepared
  2. extractionextracted with EtOAc (2×30 mL)
  3. washOrganics were washed with brine (30 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-54a4b70f9d964f5c9a5874d8e2521554
Source dataset
uspto-grants-2005_04
Patent number
US06884890B2

Reaction notes

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