Neopentyl alcohol → HCID 57424228, compound

HRID 1869883Notes

Reaction equation

HRID 1869883 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:12]([OH:14])=[O:13])[CH:11]=1)[O:8][C:7]([CH3:16])([CH3:15])[CH2:6][C:5]2([CH3:18])[CH3:17].[CH2:19](O)[C:20]([CH3:23])([CH3:22])[CH3:21].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[CH3:19][C:20]([CH3:23])([CH3:22])[CH2:21][O:13][C:12]([C:10]1[CH:11]=[C:2]([Br:1])[CH:3]=[C:4]2[C:9]=1[O:8][C:7]([CH3:16])([CH3:15])[CH2:6][C:5]2([CH3:18])[CH3:17])=[O:14]

Participants

6

Reactant 3

HCID 6404Neopentyl alcoholHCID 10868DicyclohexylcarbodiimideHCID 21107216HCID 21107216, compound2×

Product 1

HCID 57424228HCID 57424228, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A stirred cooled (ice bath) solution of 6-bromo-2,2,4,4-tetramethylchroman-8-carboxylic acid (Intermediate 41, 0.5 g, 1.6 mmol), neopentylalcohol (0.35 mL, 3.2 mmol) and 4-(dimethylamino)pyridine (0.03 g, 0.24 mmol) in anhydrous dichloromethane (5 mL) was treated with 1,3-dicyclohexylcarbodiimide (0.36 g, 1.76 mmol) and the reaction mixture was allowed to warm to ambient temperature. After 2 h, the reaction mixture was filtered, the filtrate was diluted with ethyl acetate and washed with 2N hydrochloric acid, 2N sodium hydroxide, and brine, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title product as a yellow solid (0.537 g, 88%).

Workup

  1. filtrationthe reaction mixture was filtered
  2. additionthe filtrate was diluted with ethyl acetate
  3. washwashed with 2N hydrochloric acid, 2N sodium hydroxide, and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-267c812128b64e2c8107b2b280afe447
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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