Methanol → 7-Bromo-2-methyl-2-phenylheptan-1-ol

HRID 239083Notes

Reaction equation

HRID 239083 reaction equation
BrCCCCC(C)(C1C=CC(C)=CC=1)CO.[Br:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([CH3:35])([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:24](OCC)=[O:25].[Li+].[BH4-].CO>C(Cl)Cl>[Br:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([CH3:35])([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[CH2:24][OH:25]

Participants

6

Reactant 4

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 111968926-Bromo-2-methyl-2-p-tolylhexan-1-olHCID 11313415Ethyl 7-bromo-2-methyl-2-phenylheptanoate

Product 1

HCID 113006147-Bromo-2-methyl-2-phenylheptan-1-olYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to the procedure given for the synthesis of 206e, 205h (60.0 g, 183 mmol) was reduced with LiBH4 (5.96 g, 274 mmol) and methanol (8.55 g, 269 mmol) in anhydrous CH2Cl2 (390 mL). After the typical workup, crude 206h (51.0 g, 98%) was obtained as a yellowish oil, which was used without further purification for the next step. 1H NMR (CDCl3): δ 7.25-7.08 (m, 5 H), 3.64 (d, 1 H, J=7.2), 3.50 (d, 1 H, J=7.2), 3.35 (t, 2 H, J=6 Hz), 1.92-0.95 (m, 9 H), 1.28 (s, 3 H). 13C NMR (CDCl3): δ 144.77, 128.51, 126.76, 126.21, 72.63, 43.45, 38.37, 34.06, 32.73, 28.96, 23.12, 21.59. HRMS (EI): Calcd for C14H21BrO (M+); 284.0776, found: 284.0787.

Sources & evidence

ORD record
ord-e09e2bc784134115a131bf60bd33ec84
Source dataset
uspto-grants-2014_02
Patent number
US08642653B2

Reaction notes

Loading…