Potassium Hydroxide → HCID 20311410, compound

HRID 2420284Notes

Reaction equation

HRID 2420284 reaction equation
C(C1(CC)OC2C=CC=CC=2C=C1)C.BrN1C(=O)CCC1=O.Br[C@@H:24]1[C:29]([CH2:32][CH3:33])([CH2:30][CH3:31])[O:28][C:27]2[CH:34]=[CH:35][CH:36]=[CH:37][C:26]=2[C@H:25]1[OH:38].[OH-].[K+]>C(OCC)C>[O:38]1[CH:25]2[C:26]3[CH:37]=[CH:36][CH:35]=[CH:34][C:27]=3[O:28][C:29]([CH2:32][CH3:33])([CH2:30][CH3:31])[CH:24]12

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 67184N-bromobutanimideHCID 130315432,2-Diethyl-2H-1-benzopyranHCID 70620064HCID 70620064, compound

Product 1

HCID 20311410HCID 20311410, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2,2-Diethyl-2H-benzo[b]pyran (3.86 g.) was treated with N-bromosuccinimide (7.40 g.) under the conditions described in Example 5 yielding trans-3-bromo-3,4-dihydro-2,2-diethyl-2H-benzo[b]pyran-4-ol (5.70 g.), as a pale yellow solid m.p. 75° - 77° after trituration with 60°-80° petroleum ether. Reaction of this bromohydrin (5.60 g.) with potassium hydroxide pellets (6.38 g.) in diethyl ether (300 ml.) for 4.5 days following Example 7 gave 3,4-epoxy-3,4-dihydro-2,2-diethyl-2H-benzo[b]pyran as a colourless liquid (4.28 g.) displaying signals centred at δ 3.66 and 3.78 (doublets, of coupling constant J = 4Hz) in its p.m.r. spectrum (CDCl3, with TMS as internal standard) corresponding to protons located at C-3 and C-4. Treatment of this epoxide (1.40 g.) with isopropylamine (3.50 g., an excess) and work-up as in Example 1, gave trans-4-isopropylamino-3,4-dihydro-2,2-diethyl-2H-benzo[b]pyran-3-ol hydrochloride (1.67 g.) m.p. 200° - 202°.

Workup

  1. customwith 60°-80°

Sources & evidence

ORD record
ord-1472b1ab40b741e2852ad093cbd85f49
Source dataset
uspto-grants-1978_08
Patent number
US04110347

Reaction notes

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